Clockwork wont flash, Can't get into recovery

[DroiDRN26]

I rooted my droid running 2.2 last sunday. Recent ran into an issue regarding recovery and clockwork mod.

ISSUE:
When I try to flash clockwork mod, it doesn't do anything. All i can see is the little circle that tells me it's loading or doing something. It will continually do this. I do not get an error message or anything. When I try to reboot into recovery I get the stock recovery screen and I can't get to any of the functions. If i pull the battery however it does reboot normally without issue. I wiped my phone and it got clockwork to work for a couple minutes then it went right back to the same problem. I'm not sure not to fix the problem. I tried to repair the permissions but even that didn't work/help. I'm currently using a mac right now but I do have access to a comp with windows 7.

Really what I want to accomplish is to get my phone back to fresh out of the box stock, but with not being able to get to recovery, I'm not sure I can do that right?. Any help would be greatly appreciated. Thanks

If it helps I used a program that was a one click rooting program. I remember the file being named "Soup or root" If you need any other info let me know. I did search and found one other thread on this I know it was a known problem back in august but this was before the 2.2 update, so idk if I can follow those instruction to fix this problem



EDIT: For some reason after reparing permissions, and pulling battery, it flashed CWM and I was able to reload smoked glass rom i was using before...Mmmhmm...regardless of the fix, any advice on what to do if it happens again ? Is there something that i may be running that is incompatible with something ?