I haven't tried Droid X, but Droid 2 works.

 

I've been using Bootstrap 2 and it works fine.

 

both work...but for X to work you need to turn usb debugging to 'OFF'

 

well, X bootstrap doesn't work on the odex version of .595, with USB debug checked or unchecked, so I'd go with 2

 

<<spoiler: n00b alert>>
So, I'm pretty sure that I could use either DXBS or D2BS for executing into GB. Did I get that part right? I've seen mention that, to use DXBS, I'd need to 'un-check' the box for 'USB debugging' (eg, disabled). Did I get that part? And I've seen many people state that it's just as straightforward to use D2BS. Did I get that part right? However, it wasn't clear to me what state the debugging option needs to be in (enabled vs disabled). Any insight/assistance/guidance is greatly appreciated.

I've also read that there is no direct upgrade/install path from Froyo to the leaked GB .595 (deo + root). The advice there is to install the leaked GB .588 files first, then flash to .595. Did I get that right? Again, any insight/assistance/guidance is greatly appreciated.

Lastly, I finally found the TBH app so frequently mentioned (yet more discreetly revealed - I felt like I was looking for 'ye Lucky Charms, LOL). I noted today (after yet another SBF back to Froyo - thanks 1KDS!) that the TBH app now lists .596 variants. Is it more wise to just flash the .596? Is there still the constraint of executing to .588 first then --> .595? Again, any insight/assistance/guidance is greatly appreciated.

Namast

 

droid2 bootstrapper works on all of 'em, if it were me (and this is what I did) just get D2 bootstrapper
If you're using DX bs, UNcheck the usb debugging.
If you're in FroYo .340, just take the two files for .596 and go straight there, no muss, no fuss.