Just to clarify, I don't think you're talking about budgeting software per se, it's more personal accounting software. Budgeting is a specific function that some programs do well and others not so well, but if you're talking about tracking your income and expenses you're talking about personal accounting software.
If you don't want to be locked into having to rebuy the program every year, you could check out Moneydance -- I think they're a bit better about maintaining download capability from year to year.
Also I wanted to respond to this:
I use Quicken and enter everything manually, which allows me to use the same version for years without ever having to upgrade unless they happen to add some new feature that I really want. Both Quicken and Money are very mature programs at this point, so it's hard to imagine any killer new feature that would make me want to upgrade...usually the only time I upgrade is if I upgrade my operating system and my old version of Quicken doesn't work under the new OS.
If you don't want to be locked into having to rebuy the program every year, you could check out Moneydance -- I think they're a bit better about maintaining download capability from year to year.
Also I wanted to respond to this:
I know this isn't what you want to hear, but I have a similar number of transactions per month and I find that entering them manually helps me stay on top of things better. I used to download all my transactions and found I didn't pay as much attention to my spending as I did when I switched back to doing them manually.
I use Quicken and enter everything manually, which allows me to use the same version for years without ever having to upgrade unless they happen to add some new feature that I really want. Both Quicken and Money are very mature programs at this point, so it's hard to imagine any killer new feature that would make me want to upgrade...usually the only time I upgrade is if I upgrade my operating system and my old version of Quicken doesn't work under the new OS.