Renting from self during out of area remodel project - deductible?
There are certain situations where you could legally pay yourself rent, but it'd be in the context of multiple business entities interacting, never in the context of an individual renting their own property.  Even if you could, any rent paid to yourself would count as rental income, so there'd be no benefit. Edit: I was hunting for examples where it might be acceptable, and didn't, but I found a good explanation as to why it is not acceptable from Brandon Hall on a BiggerPockets post: To get technical, you will be going up against the Economic Substance   Doctrine which states that a transaction has economic substance if:   (1) the transaction changes in a meaningful way (apart from Federal   income tax effects) the taxpayer’s economic position; and (2) the   taxpayer has a substantial purpose (apart from Federal income tax   effects) for entering into such transaction. By transferring your primary residence into a LLC, you would not be   changing your economic position. Further, you do not have a   substantial purpose for entering into such transaction other than to   simply avoid paying federal income taxes. So it might make sense if multiple people owned the LLC that owned the property you wanted to rent, and there are instances where company X owns holding company Y that owns an office building that company X rents space in. But if you're the sole player in the LLC's then it sounds like a no-go.
The rent versus buy question is a deeply personal one in which your personal desires for a living space need to be carefully combined with what makes economic sense.  Do you want your own place with all the joys of having it be yours and all the pains of having to handle all the maintenance and be the one ultimately responsible?  Have you tried living for a few months putting aside the amount required for not only a mortgage payment but the taxes and insurance on a house/condo in your price range to see if you can really afford it?  You can use a real estate website such as trulia to see the assessments of some for sale homes and figure out tax values.  The average home insurance in the US is around $900/year if I remember right - more for homes that are more expensive and less for less expensive ones, with flooding and other hazards as a factor.  Make sure you can afford to pay for all these items. From a financial perspective realize that you'll always be spending money on your living space.  Even if you pay for a house with cash you will be paying property tax and maintenance and would be wise to continue paying for insurance.  The value of the house at that point is, as contributor fennec often says, the rent you aren't paying. I personally don't recommend trying to time the market.  You can't predict the future - will real estate in your area be a double dip or has it bottomed and is it going up?  What you can do is buy a home only when you are sure that you can deal with its relative lack of liquidity by staying there for a long time.  Five years is usually a reasonable minimum.   There is a way that I recommend figuring out if it is likely bad financial decision to buy, and that's by looking at a financial comparison of renting versus buying.  In some cases even with the bursting of the bubble it is still a bad deal to buy.  DC went from renting being more cost effective to buying, but San Francisco is one area where buying is still not necessarily the best choice.  To figure out what the case is for your area, look at the New York Times rent versus buy calculator.  Find a home for rent on craigslist similar to what you'd look to buy.  Find a home for sale on one of the MLS aggregator sites that represents something you think you'd like.  Plug in the numbers.  Figure out how many years you'd have to stay in your purchase for it to be a good deal. In the likely event that the calculator says buy, start saving if that's what you really want.  You're never going to be able to absolutely guarantee that you won't be upside down.  What you can control is getting as much principal in that house as you can.  The more you have, the less likely you will be upside down.  Build a down payment now, reap the rewards later. "See this question regarding the relationship between a HDHP (High Deductible Health Plan) and an HSA (Health Savings Account). In brief, to qualify for an HSA you must have a HDHP: HDHPs are plans with a minimum deductible of $1,200 for self-only coverage and $2,400 for self-and-family coverage. The maximum amount out-of-pocket limit for HDHPs is $5,950 for self-only coverage and $11,900 for self-and-family coverage. As mentioned by Stainsor, your insurance can either come from your employer, or it can be an individually purchased plan. The HSA can be bundled as part of a package with the insurance, or it can be an account you set up separately. Contributions you make to the HSA are tax deductible. You'll report the amount you contributed when you file your taxes the following year. E.g. in April 2012 you'll report (and deduct) the amount of HSA contributions you made for tax year 2011. I'm not sure what kind of trouble you'll get into if you have an HSA without having a qualified HDHP. To answer the main part of your question: Different HSAs may have slightly different features, but I've typically seen them provide the following ways to withdraw funds: Via a debit card issued with the account. You can use the debit card to pay for things like drugs at the pharmacy, or at a doctors' office that requires payment at the time of service. Via online bill pay. You can use this to pay bills from hospitals, doctors' offices, or other healthcare service providers that send you bills. Via paper checks. For doctors' offices that require payment at time of service but don't accept plastic. (Or if you prefer not to use online bill pay.) Via withdrawal at a teller window or ATM. You can use this to ""reimburse yourself"" for healthcare expenses that you paid out of pocket. The issue of documenting legitimate expenses and/or qualifying for the account with an HDHP is between you and the IRS. The bank at which your HSA is kept doesn't really care whether you comply with the tax laws." Your freelance income will not qualify you for the work-from-home deductions, for that you would need a T2200 form signed by your employer. But, you are allowed to be self employed as a sole-proprietorship while still being an employee of another company. If you take that route, you'll be able to write-off even more expenses than those you linked to. Things like a portion of your internet bill can be claimed, for example. But note that these deductions would only apply to offset the self-employment income, so if you're not earning very much from the freelance work, it might not be worth all the hassle. Filing taxes when self-employed is definitely more complicated, and many people will get professional tax preparation help - at least for the first time. It sounds like you are doing great.  A couple points: You really need to crunch the numbers such as how high is rent in your area, and of course home prices. Home price gains are not a given. It will depend on many factors such as the job market in your area, crime, schools, how long you stay put,..etc.  If you take the standard/non-itemized tax deduction you might not save at tax time if you don't pay enough interest. Your decision to have automatic deductions from your checks was spot on; it is human nature to spend every nickle. Also, money in a savings account won't keep up with inflation. It will slowly degrade; you will want other investments.  -Good luck Do Alice and Bob have to figure out the fair market value of their services and report that as income or something? Yes, exactly that.  See Topic 420.   Note that if the computer program is for Bob's business, Bob might be able to deduct it on his taxes.  Similarly, if the remodeling is on Alice's business property, she might be able to deduct it.  There might also be other tax advantages in certain circumstances. "As @BrenBarn points out, when people say ""they like having a mortgage because they get the benefit of writing off the interest"" they typically mean as opposed to renting. You can deduct interest and real estate (property) tax payments, as well as some closing costs in the year you purchase the home. You are also building equity (instead of helping your landlord build his or her equity).  Take for example a single person paying $1,000/month to rent an apartment. This is not deductible. He has $1,800 a year in other expenditures that would otherwise be deductible (charitable contributions, etc.), but he doesn't itemize because it isn't more than the $6,100 standard deduction, so it doesn't matter.  He takes out a mortgage for $150,000 at 6% over a 30-year term to buy a similarly-appointed home. His new mortgage payment is about $900/month, plus he puts $100/month into an escrow account for property taxes, roughly totaling his former rent payment. Over the first full year, he pays about $9,000 in deductible mortgage interest and $1,200 in deductible real estate taxes. And because he is now itemizing, he can also write off the aforementioned $1,800. At a top marginal tax rate of 25%, he shaved nearly $1,500 (.25 * (9000 + 1200 + 1800 - 6100)) off his federal income tax bill -- with the same living expenses! This is a simple example with some arbitrary numbers to prove the point, and there are a lot of other pros and cons to buying vs. renting. But again, this is probably what they mean when you hear this. Others have covered the overpaying angle, and there are a bunch of other Money.SE posts on the same or similar subjects." "According to US News, renter's insurance does cover liability as well as your own belongings.  They list this as one of four ""myths"" often promulgated about renter's insurance.  This is backed up by esurance.com, which explicitly mentions ""Property damage to others"" as covered.  Nationwide Insurance says that renter's insurance covers ""Personal liability insurance for renters"" and ""Personal umbrella liability insurance"".  Those were the first three working links for ""what does renters insurance cover"" on Google.   In short, while it is possible that you currently have a different kind of coverage, this is not a limitation of renter's insurance per se.  It could be a limitation in your current coverage.  You may be able to simply change your coverage with your current provider.  Or switch providers.  Or you may already be covered.   Note that renter's insurance does not cover the building against general damage, e.g. tornado or a fire spreading from an adjacent building.  It is specific to covering things that you caused.  This may be the cause of the confusion, as some sources say that it doesn't cover anything in the building.  That's generally not true.  It usually covers all your liability except for specific exceptions (e.g. waterbed insurance is often extra)." Think carefully about the added expenses.  It may still make sense, but it probably won't be as cheap as you are thinking.  In addition to the mortgage and property taxes, there is also insurance and building maintenance and repairs. Appliances, carpets, and roofs need to be replaced periodically.  Depending on the area of the country there is lawn maintenance and now removal. You need to make sure you can cover the expenses if you are without a tenant for 6 months or longer.  When tenants change, there is usually some cleaning and painting that needs to be done. You can deduct the mortgage interest and property taxes on your part of the building.  You need to claim any rent as income, but can deduct the other part of the mortgage interest and taxes as an expense.  You can also deduct building maintenance and repairs on the rental portion of the building.  Some improvements need to be depreciated over time (5-27 years).  You also need to depreciate the cost of the rental portion of the building.  This basically means that you get a deduction each year, but lower the cost basis of the building so you owe more capital gains taxes when you sell. If you do this, I would get a professional to do your taxes at least the first year.  Its not hard once you see it done, but there are a lot of details and complications that you want to get right.