Pros and cons of using a personal assistant service to manage your personal finances?
Years ago I hired someone part time (not virtual however) to help me with all sorts of things.  Yes it helps free up some time. However particularly with finances, it does take a leap of faith.  If you have high value accounts that this person will be dealing with you can always get them bonded.  Getting an individual with a clean credit history and no criminal background bonded usually costs < $600 a year (depending on $ risk exposure). I would start out small with tasks that do not directly put that person in control of your money.  In my case I didn't have an official business, I worked a normal 9-5 job, but I owned several rental units, and an interest in a bar.  My assistant also had a normal 9-5 job and worked 5-10 hours a week for me on various things. Small stuff at first like managing my calendar, reminding me when bills were due, shipping packages, even calling to set up a hair cut. At some point she moved to contacting tenants, meeting with contractors, showing apartments, etc... I paid her a fixed about each week plus expenses. I would pay her extra if I needed her more (say showing an apartment on a Saturday, or meeting a plumber). She would handled all sorts of stuff for me, and I gave her the flexibility when needed to fit things in with her schedule. After about a month I did get her a credit card for expenses. Obviously a virtual assistant would not be able to do some of these things but I think you get the point.   Eventually when the trust had been built up I put her on most of my accounts and gave her some fiduciary responsibilities as well. I'm not sure that this level of trust would be possible to get to with a virtual assistant. However, with a virtual assistant you might be able to avoid one really big danger of hiring an assistant.... You see, several years later when I sold off my apartment buildings I no longer needed an assistant, so I married her. Now one good thing about that is I don't have to pay her now.   ;) "Not knowing anything about your situation or what makes it so complex, I would have to agree with the other commenters.  If your accountant screws up your business goes under, but at least your personal finances are safe from that and you'll recover (unless all your wealth is tied up in your business).  If your virtual assistant uses your personal information to take all your money, ruin your credit, or any number of other things, you're going to spend a loooong time trying to get things ""back to normal"". If the few hours per month spent managing your finances is starting to add up, I might suggest looking into other ways to automate and manage them.  For instance, are all of your bills (or as many as you can) e-bills that can be issued electronically to your bank?  Have you set up online bill pay with your bank, so that you can automatically pay all the bills when they arrive?  Have you tried using any number of online services (Mint, Thrive, your bank's ""virtual wallet/portfolio"") to help with budget, expense tracking, etc.? Again, I don't know your exact situation, but hopefully some of these suggestions help.  Once I started automating my savings and a lot of my bill paying, it gave me a lot of peace of mind." When you want to hire personal assistants, you must be sure that you are hiring in a trusted company or the person you talk to have been proven by a lot of people. You must be wise in choosing one because these people will handle some of your personal things and data.
"Two types of people: (1) Suckers (2) People who feel that investment advisors/brokers make too little money and want to help out by paying insane commissions. Think I'm kidding. Check out this article: ""Variable Annuity Pros and Cons"" Seriously, for 99% of us, they are a raw deal for everyone except the person selling them." "It's a decision that only you can make. What are the chances that you'll want to take another loan (any loan - car, credit card, installment plan for new fridge, whatever else)? What are the chances that with the bad credit you'll find it hard to rent a place (and in Cali it's hard to rent a place right now, believe me, I bought a place just to save on the rent)? What are the chances that the prices will bounce and your ""on-paper"" loss will be recovered by the time you actually need/want to sell the house? You have to check all these and make a wise decision considering all the pros and cons in your personal case." Is it worth saving HSA funds until retirement? Yes Are there pros and cons from a tax perspective?  Mostly pros. This has all of the benefits of an IRA, but if you use it for medical expenses then you get to use the money tax free on the other side. Retirement seems to be the time you are most likely to need money for medical expenses. So why wouldn't you want to start saving tax free to cover those expenses? The cons are similar to other tax advantaged retirement accounts. If you withdraw before retirement time for non-medical purposes, you will pay penalties, but if you withdraw at retirement time, you will pay the same taxes you would pay on an IRA. I should note that I put my money where my mouth is and I max out my contribution to my HSA every year. "Unfortunately I don't think any of the online personal finance applications will do what you're asking. Most (if not all) online person finance software uses a combination of partnerships with the banks themselves and ""screen scraping"" to import your data. This simplifies things for the user but is typically limited to whenever the service was activated. Online personal finance software is still relatively young and doesn't offer the depth available in a desktop application (yet). If you are unwilling to part with historical data you spent years accumulating you are better off with a desktop application. Online Personal Finance Software Pros Cons Desktop Personal Finance Software Pros Cons In my humble opinion the personal finance software industry really needs a hybrid approach. A desktop application that is synchronized with a website. Offering the stability and tools of a desktop application with the availability of a web application." Some accounts, such as my electric, and payments to the tax collector charge a significant enough fee that is counter productive to use a rewards card.  One example of this is Alligent Air.  They give you a $6 discount if you pay with a debit card which was about 5% of the ticket price. Anytime you borrow money, even as well intentioned and thought out as you plan to do so, you are increasing risk.  By managing it carefully you can certainly mitigate it.  The question becomes, does that time spent in management worth the $600/year? I did the costco amex deal for about 12 years earning about $300-$400 per year and only once getting hit with a late/finance charge.  Despite the success, I opted to end this for a few different reasons.  First off people using credit tend to spend more.  Secondly, I felt it was not worth my time in management.  Thirdly, I did not want the risk. Despite the boasts of many, the reality is that few people actually pay off their card each month.  By your post, it seems to me that you will be one of the rare few.  However, if you are expending 5K per month, your income must be above the US national average.  Is $600 really worth it? Perhaps budgeting for Christmas would be a better option. "Technically, anyone who advises how you should spend or proportion your money is a financial adviser.  A person that does it for money is a Financial Advisor (difference in spelling). Financial Advisors are people that basically build, manage, or advise on your portfolio.  They have a little more institutional knowledge on how/where to invest, given your goals, since they do it on a daily basis. They may know a little more than you since, they deal with many different assets: stocks, ETFs, mutual funds, bonds, insurances (home/health/life), REITs, options, futures, LEAPS, etc. There is risk in everything you do, which is why what they propose is generally according to the risk-level you want to assume.  Since you're younger, your risk level could be a little higher, as you approach retirement, your risk level will be lower.  Risk level should be associated with how likely you're able to reacquire your assets if you lose it all as well as, your likelihood to enjoy the fruits from your investments. Financial Advisors are great, however, be careful about them.  Some are payed on commissions, which are given money for investing in packages that they support.  Basically, they could get paid $$ for putting you in a losing situation.  Also be careful because some announce that they are fee-based - these advisers often receive fees as well as commissions.  Basically, associate the term ""commission"" with ""conflict-of-interest"", so you want a fee-only Advisor, which isn't persuaded to steer you wrong. Another thing worth noting is that some trading companies (like e*trade) has financial services that may be free, depending how much money you have with them.  Generally, $50K is on the lower end to get a Financial Advisors.  There has been corruption in the past, where Financial Advisors are only given a limited number of accounts to manage, that means they took the lower-valued ones and basically ran them into the ground, so they could get newer ones from the lot that were hopefully worth more - the larger their portfolio, the more $$ they could make (higher fees or more commissions) and subjectively less work (less accounts to have to deal with), that's subjective, since the spread of the wealth was accross many markets." My bank will let me download credit card transactions directly into a personal finance program, and by assigning categories to stores I can get at least a rough overview of that sidd of things, and then adjust categories/splits when needed. Ditto checks. Most of my spending is covered by those. Doesn't help with cash transactions, though; if I want to capture those accurately I need to save receipts. There are ocr products which claim to help capture those; haven't tried them. Currently, since my spending is fairly stable, I'm mostly leaving those as unknown; that wouldn't work for you. "Be very careful with this.  When we tried this with furniture, they charged an ""administrative"" fee to setup the account.  I believe it was about $75.  So if you defer interest for one year on a $1000 purchase and pay a $75 administrative fee, it's 7.5% interest. Also, they don't always send you a bill when it's due, they just let you go over the date when you could have paid it without paying interest, and then you owe interest from the date of purchase.  These plans are slimy.  Be careful."