I don't know really how easy it is, I know there were reports of screwing things up and needing backups before but perhaps those issues have been sorted. Something like the 900 series (950 or 960) is quite affordable and uses the older dedicated interface, as is the DDA-125 (I think the 120 and lower have CRTs) - a bit obtuse in terms of layout for my tastes, but powerful and responsive. Newer scopes of theirs, the WavePro 7000/8000 series and DDA/SDA/WaveMaster equivalents are pretty powerful Windows 2000/XP based scopes that have had a fair bit of hacking and analysis done on the forum. Beyond that, and likely still in your budget, are the more modern smaller form factor scopes. You'll pay a fair bit more for the small form factor and newer model, but the base scope interface will be basically the same (X-Stream software on all their windows based scopes and some more modern non-windows ones), and you can still get a good amount of bandwidth for your buck.
At least for the older, larger form factor scopes, they can be a bit noisy for fans, but it's not awful and can be improved with high flow replacements. Since they're basically just a microATX PC in a scope chassis on the windows models, it's pretty easy to upgrade to the max of the board for a bit better responsiveness/load times, and some upgrades of the mainboard to a whole new chipset (or to windows 7) have been documented in some threads around. I've worked with a DDA-125, WavePro 960, WavePro 7200, and WavePro 7300A and have found them all to be pretty nice scopes, the first two with the older display format and OS, the remaining two with windows and X-Stream, and the only real quirk of an issue is that on the 7300A, I get a relay click and recalibration (temperature compensation, presumably) on every new acquisition not in roll mode, which is really obtuse. In another thread it was mentioned that this was common and expected by some users, but my WP7200 never did that - just the occasional temperature compensation every few minutes like a SA alignment or similar, so I expect it can probably be figured out, I just haven't mucked around in the calibration menu to try and fix it myself, yet.
In the case of any of those, there are a good number of units for sale with software options unlocked, but hacking if effective would take care of that, though the acquisition memory options are hardware based and are not software unlockable (it seems that very large memory options may even use different ADC boards that are larger for the extra memory chips).
In any case, I'm sure there are some complaints with them, but for high bandwidth 8 bit scopes that offer a lot of bang for your buck, these used LeCroys have seemed like the best value proposition for a while now. I'd expect a WP950 to start a bit more than $1000US, with WP7200s closer to $2000, but there are sometimes deals floating around especially if you don't mind risking buying an untested unit.