What headaches will I have switching from Quicken to GnuCash?
I have not used Quicken; I've used GnuCash exclusively.  It feels a bit rough with the UI: Balancing that, the data is stored in a gzip-compressed xml file. The compression is also optional, so you can save it as a plain xml file.  This means that you have some hope of recovery if you wind up with a corrupted file. (And for programmer-types, you could keep it in source control for additional peace of mind.) My wife and I have been using it for several years now, and has worked well for us. LWN.net had a pair of Grumpy Editor reviews on personal finance software here and here which would be worth reading. The best way to answer this question is to try. GnuCash is free, so setting it up and giving it a go shouldn't be too hard. After all, what really matters is how helpful the program is for your purposes. One aspect of personal finance that stops me from jumping to GnuCash/KMyMoney/MoneyDance is the ability to download transactions from my financial institutions. Last time I checked, the process was somewhat involved and support was limited for a handful of banks. Because of that, I decided to stick with MS Money (and once Microsoft dropped the ball, with Quicken). I am sure things are better these days, but I am still not comfortable with trusting my finances to something new and unproven. I still remember how painful it was several years ago, when some bug in MS Money caused occasional mess-up of the reconciliation state for the American Express credit cards. It's been a long time since I've used MS Money and/or Quickbooks (never Quicken), but I've used GnuCash over the past year or so. It works, but it does suffer from some usability problems. Some of the UI is clunky. Data entry sequences are a little harder than they should be. Reports could be a little prettier. But overall it does work, and it's the best I've found on linux. (I would definitely appreciate pointers to something better.) Instead of gnucash i suggest you to use kmymoney. It's easier
Perhaps you should use your own tracking software, such as GnuCash, Quicken, Mint, or even Excel.  The latter would work given you say you're manually putting in your transactions.   There's lots of pre-done spreadsheets for tracking investments if you look around.    I'm hoping that a web search gets you help on migrating transaction data, but I've yet to run into any tools to do the export and import beyond a manual effort.  Then again, I haven't checked for this lately. Not sure about your other questions, but I'd recommend you edit the question to only contain what you're asking about in the subject. "Changes in graduated income tax rates don't necessarily drive how you should allocate money to a Traditional vs Roth account (true for both IRA or 401k). What does drive this decision is what your income tax rate is now compared to what you believe your rate will be when you retire. So, if you expect the tax rate change to still be in effect when you retire, it doesn't matter if the change is a tax increase or decrease; your previous allocation could likely remain the same. This means that if Congress passed the change effective immediately, it would be too late for you to make a meaningful adjustment. But if Congress passes the change effective next year, then most likely your tax rate will decrease for next year, meaning you are probably better off switching all Roth allocations to Traditional, and then switching them back to whatever allocations you have now for next year. The reverse would be true if you knew about an upcoming tax increase (in which case you would load up Roth this year and then switch back to whatever you had for next year). That being said, regarding after the fact reallocation considerations, I suppose it would be fair to say that if the country is accustomed to a higher tax rate, and then rates are dropped, if spending is not cut to make up for it, then rates would likely have to go up again in the future to make up the difference. If you believe that will happen then Roths would become a little more attractive since rates would be lower than what you expect them to be when you retire. As a side note, if you ever had reason to believe that Congress was going to move away from the ""graduated income tax"" structure, all bets are off. For example if the income tax was replaced with a tax on spending such as the FairTax, then in the interim period Roths would become worthless and you'd want to switch to Traditionals until the change went into effect. (And then once in effect both Roths and Traditionals would be pointless.)" The committee folks told us Did they also give you advice on your medication? Maybe if they told you to take this medicine or that you'd do that? What is it with people taking tax advice from random people? The committee told you that one person should take income belonging to others because they don't know how to explain to you which form to fill. Essentially, they told you to commit a fraud because forms are hard. I now think about the tax implications, that makes me pretty nervous. Rightly so. Am I going to have to pay tax on $3000 of income, even though my actual winning is only $1000? From the IRS standpoint - yes. Can I take in the $3000 as income with $2000 out as expenses to independent contractors somehow? That's the only solution. You'll have to get their W8's, and issue 1099 to each of them for the amounts you're going to pay them. Essentially you volunteered to do what the award committee was supposed to be doing, on your own dime. Note that if you already got the $3K but haven't paid them yet - you'll pay taxes on $3K for the year 2015, but the expense will be for the year 2016. Except guess what: it may land your international students friends in trouble. They're allowed to win prizes. But they're not allowed to work. Being independent contractor is considered work. While I'm sure if USCIS comes knocking, you'll be kind enough to testify on their behalf, the problem might be that the USCIS won't come knocking. They'll just look at their tax returns and deny their visas/extensions. Bottom line, next time ask a professional (EA/CPA licensed in your State) before taking advice from random people who just want the headache of figuring out new forms to go away. Ally Bank is a good online only account.  They reimburse any ATM Fees you may occur.  I have both checking and savings, with both Ally and ING Direct.  I don't know about having 25 total accounts - seems like overkill to me.  I do something similar though - I get direct deposit into one account, then transfer the average bill amount each pay to a different account that I never touch other than for the allotted bills.  It works well, especially for Utilities that are inflated seasonally. What do you use to mange the 25 accounts?  I use Quicken, but I don't have 25 accounts...yet. 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. My possible new job requires me to do dfast and ccar among others.  A few questions   1) My background is public accounting and tax. I noted that these jobs requires experience from public firms. My past experience has nothing to do with banking. Any reasons? I have been reading up dfast in the past week and it seems they trust me to pick up fast. Another job ad from another bank indicates the same thing.   2) What type of job this is under? I tried risk analyst but quite a lot of times the results are quite different from what my job is.  3) What is the job outlook? My eventual plan is to a more data analyst role and/or job opportunities in EU. Currently in EA/SEA market.   4) Any programming language should I learn to speed up data extraction? I will be learning either python/r. And will surface 3 do? My current laptop is not working and the repair shop indicates the costs of repairing doesnt worth it. "I definitely get where you're coming from.  The envelope system sounds good, but doesn't appeal to most people under 50 for many of these reasons (physical cash in my hand is just a hassle - it has no appeal or reduced spending affect on me). There are various options for prepaid debit cards such as https://www.netspend.com/ or you could use gift cards for things like gas and groceries (though that likely won't get you duplicate cards or automatic payments).  As far as automatic payments, just set that up through your bank. So it's still not a perfect solution.  I wish there was a better, more straightforward way, but this is the best as far as I know. Update: Ramsey solutions has since launched EveryDollar.  This is Dave's preferred solution for an online ""digital envelope system""." Are you sure about either of those? PayPal owns Braintree which can accept Bitcoin, but I've never seen the option in PayPal itself, and I've looked, though not recently.   I've also not noticed PayPal in HD, but maybe I'm just not observant. Is that in all their stores?