GnuCash register reimbursements
You should be recording the reimbursement as a negative expense on the original account the expense was recorded. Let's assume you have a $100 expense and $100 salary. Total $200 paycheck. You will have something like this In the reports, it will show that the expense account will have $0 ($100 + ($100)), while income account will have $100 (salary).
The best way to answer this question is to try. GnuCash is free, so setting it up and giving it a go shouldn't be too hard. After all, what really matters is how helpful the program is for your purposes. One aspect of personal finance that stops me from jumping to GnuCash/KMyMoney/MoneyDance is the ability to download transactions from my financial institutions. Last time I checked, the process was somewhat involved and support was limited for a handful of banks. Because of that, I decided to stick with MS Money (and once Microsoft dropped the ball, with Quicken). I am sure things are better these days, but I am still not comfortable with trusting my finances to something new and unproven. I still remember how painful it was several years ago, when some bug in MS Money caused occasional mess-up of the reconciliation state for the American Express credit cards. Mint has worked fairly well for tracking budgets and expenses, but I use GnuCash to plug in the holes. It offers MSFT$ like registers; the ability to track cash expenses, assets, and liabilities; and the option to track individual investment transactions. I also use GnuCash reports for my taxes since it gives a clearer picture of my finances than Mint does. "I've been in a very similar situation to yours in the past.  Since the company is reimbursing you at a flat rate (I assume you don't need to provide documentation/receipts in order to be paid the per diem), it's not directly connected to the $90 in expenses that you mention.  Unless they were taking taxes out that would need to be reimbursed, the separate category for Assets:Reimbursable:Gotham City serves no real purpose, other than to categorize the expenses. Since there is no direct relationship between your expenses and the reimbursement, I would list them as completely separate transactions: Later, if you needed to locate all of the associated expenses with the Gotham trip, gnucash lets you search on memo text for ""Gotham"" and will display all of the related transactions.  This is a lot cleaner than having to determine what piece of the per diem goes to which expenses, or having to create a new Asset account every time you go on a trip." I use GnuCash which I really like.  However, I've never used any other personal finance software so I can't really compare.  Before GnuCash, I used an Excel spreadsheet which works fine for very basic finances. Pros Cons Is that really a surprise? Merchant fees are typically around 2-3% (article says 1-4%) of the transaction sometimes with per transaction fees too. However, if you are paying 4% get a new CC processor. I am paying 2.75% for swiped/chip transactions for almost no volume with Square (I don't sell much, have it for convenience just in case).  https://squareup.com/pricing  I would be willing to bet that the ratio of overdrafts compared to not overdrafts is very low. I know I can't use my visa debit card when there is no money in the bank, and really, how many people use checks anymore? "This is the best tl;dr I could make, [original](http://fortune.com/2017/07/06/coinbase-irs-summons/) reduced by 68%. (I'm a bot) ***** &gt; &amp;quot;DOJ trial attorney Amy Matchison said at a court hearing before U.S. Magistrate Judge Jacqueline Scott Corley Thursday that the IRS has been in talks with Coinbase about narrowing its request to only items the agency would need to look for unreported income,&amp;quot; reported The Recorder, a legal site that reported on the hearing.  &gt; The agency has stated that only 802 people declared gains or losses related to bitcoin in 2015.In a email, Coinbase declined to comment on the IRS&amp;#039;s reported decision not to seek passwords, and referred Fortune to a blog post from March in which the company said it is pushing the agency to reduce the scope of the probe.  &gt; When news of the IRS probe first emerged, some legal observers predicted the agency&amp;#039;s demands for all of Coinbase&amp;#039;s customer records was just a negotiating tactic, and that it would ultimately ask for only a portion of them.   ***** [**Extended Summary**](http://np.reddit.com/r/autotldr/comments/6lsekz/irs_says_it_will_limit_bitcoin_auditsbut_only_a/) | [FAQ](http://np.reddit.com/r/autotldr/comments/31b9fm/faq_autotldr_bot/ ""Version 1.65, ~161341 tl;drs so far."") | [Feedback](http://np.reddit.com/message/compose?to=%23autotldr ""PM's and comments are monitored, constructive feedback is welcome."") | *Top* *keywords*: **Coinbase**^#1 **IRS**^#2 **agency**^#3 **customer**^#4 **account**^#5" W9 is required for any payments. However, in your case - these are not payments, but refunds, i.e.: you're not receiving any income from the company that is subject to tax or withholding rules, you're receiving money that is yours already. I do not think they have a right to demand W9 as a condition of refund, and as Joe suggested - would dispute the charge as fraudulent. Street name is not what you think it is in the question.  The broker is the owner in street name.  There is no external secondary owner information.   I don't know if there is available independent verification, but if the broker is in the US and they go out of business suddenly, you can make a claim to the SIPC.