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Starting to have a few minor issues and not sure where to begin. Running Droid 2 with 2.5.7 Black and Gongerbread. Can I reflash without losing settimgs? What does clearing cache do? How and again would I lose settings?
Flashing is returning your phone to just like it was out of the box. Wiping will remove everything from the phone. Your contacts and apps will sync through google so there is nothing to worry about.
I think that if you flash it without wiping data and cache, you may not lose any of your apps, settings, or data, but if you were having problems before, there's a good chance this won't do anything to solve your problems.
What kind of problems were you having, specifically?
It really isn't such a big deal letting Google restore your apps and contacts after reflashing from scratch (wiping data and cache). You can backup and restore your text messages using SMS Backup & Restore (from the market).
The reboot problem is a widely reported issue across various ROMs (including stock, I think) on the Droid 2. Unfortunately, I really highly doubt that reflashing Fission will fix it.
Don't know about the other problem though. I assume you're talking about e-mail. What e-mail client are you using?
I don't use MMS myself, so I can't really help you. But have you tried using an alternate SMS client? If you've been using the stock messaging client, for example, try Handcent SMS and see if that does what you want it to do.
I was merely suggesting that you try a different text messaging app, not a whole different ROM. Not that you shouldn't go out and try different ROMs, of course, but if all you want is a fix to your messaging problems, try Handcent SMS (which I use, but there are others too, like Chomp SMS and Go SMS). Like I said, I don't use MMS (multimedia messaging, e.g. pictures) myself so I'm not saying that using a different SMS app will solve your problems, I'm just saying it might and is worth a try.
If you want to try another ROM, I would suggest waiting for the final release of Liberty 2.0, which should be just around the corner.
What ROM are you thinking of flashing? The instructions are usually posted in the release thread. Most ROMs are released as flashable ZIP files that you can flash in ClockworkMod Recovery.
Like I said, the final release of Liberty 2.0 is just around the corner. I would suggest waiting for it.