Hi Jesse, I've been using YNAB since the middle of 2006 and recently downloaded an evaluation copy of Pro. I've been using it consistently, but not always in exactly the way intended. It took me a long time to build up a buffer, so for the first year & a half I entered all income as supplemental. I waited until downloading the trial version of Pro and the new year to start entering income as Primary, even though I was in a position to do so at least 6 months ago.
Although I understood the basic rules, I admit there are some things that really confused me a lot at first. Since I see on the YNAB forums you're writing a new setup guide, I'll mention those here:
1. The most confusing thing was not entering payments to my credit card, since if you do so, you end up double counting expenses. To my mind, you can't emphasize this point enough! It took me months to figure this out.
2. I've never really understood about Transfers from savings (and in fact I don't even see them in Pro). The new setup guide could be a bit more explicit on how to handle Transfers from existing savings--are they income or not?
3. It took me a while to grasp the idea of making negative entries to outflw rather than positive entries to inflow when one does a return or gets a rebate/reimbursement. More info on that would be helpful.
I use YNAB because I like tracking my expenses in detail. That said, for the first 6 months of 2007 I was using a competitor product, Make$cents, which I found a bit more intuitive to use because (a) it had account balances and could balance one's checkbook; (b) the graphical interface showing little mini-envelopes rather than just a line with a balance is strangely compelling. I switched back when my old computer died because I wanted to be on the Excel platform (and I'm only upgrading to Pro because I can cut & paste the info into Excel)--being stuck on a proprietary platform is difficult when one's computer crashes--plus Excel lets me generate all kinds of custon reports & graphs.
I love the product, but I think improving the setup guide to handle these confusing points may help with people using it, at least a little. Having the automatic download from banks will also help since having to enter data by hand is a time swamp that also provides a barrier to continued use. But there will always be some resistance--behavior change is hard!
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