I notice you haven't gotten any responses yet, I just wanted to throw in my two cents and tell you the PRS-700 was definitely worth the upgrade from my old PRS-500. I know there was a bump in processor speed between the 500 and the 700 and I think the 505 uses the same processor as the 500. In short, I no longer experience that hellish waiting period of loading time when I first load a new RTF or PDF doc. RTF loads in about two seconds for an average 300 to 500 page book in first load and is instant in subsequent loads. And I haven't noticed any lag in loading PDFs at all. In addition, I have two 2Gig cards in the thing right now (one Mem Stick Duo and one SD card) and there wasn't that other hell lag when trying to turn the book on the first time after loading a few hundred books onto the card.
All in all I would definitely suggest you upgrade to the 700, I don't know the other eBook pros and Cons from as personal level as the only other eBook readers I have ever used are the eBookwise eBook Reader (Can't remember the name off hand) and its big colour screen version.
I don't know about CHM format, but I have just literally dropped RTF and PDF files into the right folder on the memory card without ever using the software and it works just fine so that would solve your OS issues to some extent, plus the 700 now includes the ability to delete eBooks from the reader with no external computer interaction which was, IMHO, sorely lacking from earlier versions.
In Short, yes Upgrade from your 505 if you can, that slow lag time between page turns and book loads was hell and I know the 700 has fixed that problem and I'm betting most other current version readers are up to 'speed' as well, or at least I would hope so.
Good Luck and happy shopping!
-Shade
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