Medical Bill Consolidation
There are definitely ways to retroactively consolidate medical bills -- there's an entire industry of companies offering debt consolidation (many of which are scummy/predatory, be careful! See https://www.consumer.ftc.gov/articles/0150-coping-debt and some decent articles at http://blog.readyforzero.com/are-there-legitimate-debt-consolidation-loans and http://blog.readyforzero.com/how-to-find-a-reputable-debt-consolidation-company). In general, what you are looking to do is take out a loan, possibly at a better interest rate than whatever you are being charged currently, and pay off the medical bills. If you are not paying interest on the medical bills and are just being allowed to spread out the payments, you are already golden and should just put up with the ups and downs. If you have any equity in a home, take out a home equity loan or line of credit, pay off your medical bills. Rates are still great right now. Even if you have no home equity to tap, if you have a steady job you might be able to get a nice small loan from a local bank or peer-to-peer lending site. Do your homework and only work with reputable companies, especially if doing things online. In short, no, or not retroactively. There really are multiple companies involved, each of which bills you separately for the services they provided. This can be partly avoided by selecting either a high-end health plan with lower out-of-pocket maximum, (costs more up front, of course) or by selecting a genuine Health Management Organization (not a PPO) which gathers more of the services into a single business. Either of these would result in fewer cash payments needing to be sent.  But I don't know of any way to simplify things after the fact. Even if there was a consolidation service, you would have to forward the bills to them, which really wouldn't be any easier than just paying the bills. (I'm assuming you are in the US, where we have a health insurance system rather than a health system. Other countries may handle this differently.)
Regarding your specific types: If you can't part with anything, sure, scan them. Also, there are lots of opportunities to sign up for eStatements with just about any financial provider.  They want you to sign up for them, because it reduces their expenses. If you still like having paper around (I do admit that it's comforting in a way) then you can usually prune your paper a bit by statement (getting rid of T&C boilerplate, advertisements, etc.) or by consolidation (toss monthly when the quarterly consolidation statement arrives; toss the quarterly when the yearly arrives). "These agencies consolidate your debt and make it an easy monthly instalment for you. They also try to negotiate with credit cards. They do so for a fee. Other option is to not pay the debt. During this time , expect credit cards to keep sending you bills and reminders and ways to contact you. Once it is not paid for a significant amount of time ( 18 months ) , the lender will ""sell"" your debt to a collection agency. You will start getting bills from collection agencies. Collection agencies can settle for up to 40 % of the actual debt. So if you had 5 credit cards , you would have 5 different collection agencies trying to get in touch with you. You can call them and tell them that you cannot pay the full amount. They will offer you settlements which you can accept or decline. The longer the unpaid debt , the more the discount they will offer. One very important thing to remember is that the unpaid amount will be sent to you on a 1099-c form . This means you have to recognize this as income. It is applicable to the year when the debt is settled. In a nut shell , you owe 120,000. You don't pay. Credit cards keeps calling you. You don't pay. After 12-18 months , they handover your debt to collection agencies. Collection agencies will try to get in touch with you. Send you lawsuit letters. You call and settle for say 50,000. You pay off 50,000 in 2016. Your debt is settled. But wait you will get 1099-C forms from different agencies totaling 70,000 ( unpaid debt ). You will have to declare that as income and you will owe tax on that. Assuming say 30 % tax you will have to pay up 21,000 as tax to IRS assuming no other income for simplicity. SO what you did was pay up 50 + 21 = 71,000 and settled the debt of 120,000. Your credit score will be much better than if you never paid at all." "The presenter suggested we keep records of our claims for 10+ years in paper form. This seemed to be overkill. It would be overkill if you're taking distributions regularly and you have enough valid (and otherwise unreimbursed) medical receipts each year to correspond to your distributions. However, if you are pumping money into the HSA without regular distributions, then you may need to keep receipts for a long time, possibly since the beginning of your HSA. For example: If the IRS was to audit my HSA deductions would the Aetna online claims be adequate? It's better than nothing, but it is not ideal. You need to provide proof of what you actually paid, not just what was billed. (How would the IRS know if you actually paid the bill?) So, the bill and receipt together would be preferred. Also, there are many eligible expenses for HSA that would not be covered by your health insurance and would not appear in your Aetna statements (dental work for example). Personally I have an excel spreadsheet with every eligible expense listed, every contribution and distribution I make, and a box of receipts since I opened the HSA account. Should I also archive screenshots of these claims digitally somewhere? If you have the time and diligence to do it, then it wouldn't hurt. I personally am only one house fire away from having to make a lot of phone calls if I wanted to re-build my receipts folder from scratch. I actually have ""scan my HSA receipts"" on my todo list (where's it been for years as a pretty low priority). Lastly it makes sense to spend the money in my HSA on anything eligible because you can never roll it over into a retirement account, its shaky if another person (spouse) could get reimbursed for eligible medical expenses if you die, and if you lose your receipts you may not be able to spend all of the HSA money tax free. Is this an accurate assessment or is there a reason why I should not touch the HSA money at all and wait to reimburse my eligible expenses. First off, if you are married the HSA can be transferred to your spouse. But in general, it really depends on what you would do with the money if you distributed it right away. If you need the money to pay debts, bills, etc, then it might make sense to take it, but if it would be extra money that you would invest somewhere, then you should leave it in the HSA because it grows tax free while it's in there and (probably) wouldn't if you take it out. The caveat though is that you need to find an HSA administrator that offers your preferred investment choices. As for your worry that you might lose your receipts, well, that's a valid point- but I wouldn't drive my decision based on that- I would archive them digitally to remove that concern completely. ...Should I reimburse myself from ... the HSA funds if I am not hitting the 401k limit yet? It depends. If it's a Roth 401k, all other things being equal, (you are able to choose the same investments with your HSA as you can choose in your 401K, and the costs are the same), then you are better off leaving the money in your HSA rather than pulling it out and putting it into the Roth 401k. The reason is that there is no tax difference, and once you put it into the 401K you (probably) can't touch it (for free) until you retire. With the HSA, if you could have taken a distribution but chose not to, then you can take that amount of money out anytime you want to without any consequences, just like your normal checking account. However, if you have a traditional 401k, and if taking HSA distributions would increase your cash flow such that you could afford to contribute more to the 401k, then this would lower your tax burden that year by reducing your taxable income." Sometimes I think a question like this is one of moral versus legal.  The reality is that you know you owe the money because you received the services.  You're right that the bill should have been sent to you, and the natural urge for many people is to just count it in the win column when things like this happen and there's the chance to avoid paying. I suppose my question for you is, are you comfortable with the notion that you are not paying something that your heart of hearts tells you should be paid?  If roles were reversed and you, as a business owner, had forgotten to bill something for which you were rightfully due payment, wouldn't you hope they'd have the integrity to pay you anyway? The legal side of this can be a bit trickier, and much depends on the state you're in (assuming you're in the U.S.) because some have stiffer consumer collection and protection laws than others.  The rehab center could, when doing an audit of its accounts, discover that you didn't pay for these.  They could take the polite course of action and call you with a gentle reminder or send a bill, or they could be not so nice about it.  Either way, they can't send anything to collections for which you haven't been presented a bill and demonstrated an unwillingness to pay.  There's a process in place, regardless of the state, so they can't just automatically put it into collections. I will close with this question for you: did the rehab center help you with what you needed, and are you healthier and better because of their care?  If so, pay the bill.  That's my advice.  Keep in mind that unpaid medical costs just raise the prices for everyone else, because these providers will make up for the loss somewhere. I hope this helps. Good luck! I think the biggest issue here is why are employees still dependent on their jobs to order to receive health care? Why should businesses be responsible for providing this?   What needs to happen in order for us to free businesses from this burdensome requirement? Single payer? Insurance sales across state lines? The number one problem here is cost of medical plans, how can that be lowered? To add to @bstpierre's answer, you should automate all your loans except for the one with the highest interest rate.  Leave that one manual, and pay the most you can afford each month, to pay it off as quickly as possible.  Once you finish that loan, move to the next highest interest rate.  Ultimately, this won't be quite as convenient as just having 1 loan.  The differences are: You need to set up all the automatic payments.  This is probably comparable to in complexity of consolidating your loans. Each time you finish one loan, you need to turn off an automatic payment, and start doing the next loan manually. If you organize yourself well initially, you'll know exactly what order to do the loans in, so this shouldn't take too long. However, unless your consolidated loan has the same interest rate of your cheapest current loan, you will likely save money over-all by using this method. My attempt to convey the shorthand report notes on file:    &gt;...bipartisan opposition at the capitol to the GOP health care bill. All three members of Vermont's congressional delegation joining the Republican Governor, and Republican and Democratic leaders of the state house and senate, all joining forces here to attack this new GOP bill...  It would send the budget into deficit or throw 51,000 Vermonters off health care completely.      &gt;The proposed deductions in Medicaid would leave our state with a budget deficit because  [we can't] absorb without cutting health services for the people who deserve it the most or significantly raising taxes... If you have heart disease, or get cancer, and are suddenly thrown off of health insurance... it is immoral, it's not acceptable.    &gt;Now it is rare to see leaders from all three parties speak out so forcefully here. Governor Scott, in particular, pleading with the Senate to slowdown, take a breath and draft something acceptable to both parties. He is back from a weekend in which he met with his fellow Republican governors, and said that many of the fellow GOP leaders feel as he does. Even conservative... minority leader Donald Turner, who supports health care reform said the Senate GOP repeal bill is not the answer. Some leaders saying the Medicaid cuts could force a number of our small rural hospitals to close. Because collective bargaining by the gov't and your employer is the only way that we've been able to combat some of the increases. An uninsured individual will be billed 4-10x what your insurance company would pay due to collective bargaining.  The largest employers (Cisco, EMC, and others) are self-insured and pay health care providers to administer their plan. SMBs get the short end of the stick and pay much higher rates for less coverage because they don't have economies of scale.   A public option would allow any uninsured individual to obtain health care at a reasonable, income-based cost.