Whatever you do, don't pay some 'computer guy' $80/hour to do this. It's a 20-minute job you can handle yourself. There are step-by-step guides all over the web with screenshots. Save your money for a faster modem or more RAM.

I learned the hard way to always back up before messing with this kind of thing. Burn a CD-R of anything important first. It takes 10 minutes and could save you from losing everything if something goes sideways.

I've been using computers since the early 90s and the answer to this has changed dramatically over the years. Right now, the best approach is to use open source alternatives when possible — they're usually free and often better than commercial products.

First thing I'd do is reboot and try again. Sounds dumb but you'd be amazed how many 'tech problems' fix themselves with a restart. If that doesn't work, write down the EXACT error message and search for it — somebody on Experts-Exchange or a Geocities help page has hit the same thing.

My advice: don't overthink it. Pick the option that works best for your situation right now. Technology changes every 2-3 years anyway so nothing you choose today is permanent. The best technology is the one you actually use.