quietgirll,
I think you'll be happy with the trolley. Considering the rest of your trip will involve lots of walking, this will give you a break from adding more walking.
If you want to relax and take it slow before you hit Orlando, I'd do 2 days if it won't cut into the rest of your trip too much.
You might have already checked out this website, but I'll give it to you just in case:
http://www.oldcity.com
I think it's one of the better sites for St. Augustine.
The Flagler tour is a guided tour done by students. It really isn't very long, but it was interesting. We also enjoy hitting the shops, popping into some of the local bars for a drink etc. We usually take it pretty easy while we are there and just do things at a slow pace.
As far as places to stay, if you want to splurge, we love the Casa Monica. If nothing else, and you enjoy a cocktail, stop in the bar and have a drink. It's a beautiful old hotel. Also, just so you are aware, all the rooms in this hotel are non-smoking. (just wanted to throw that in, not sure if that would be a concern for you or not) This is our favorite place, and even though I'm a smoker, we still pick this most often. It's romantic and we love the restaurant, 95 Cordova.
If the Casa Monica is not what you are looking for, and you'd like to try a great B & B, I'd go with Our House. Its gay owned and wonderful. The site is:
http://www.ourhousestaugustine.com
Other places we have enjoyed are the St. George Inn, which is right in the heart of St. George Street.
The Hilton St. Augustine Historic Bayfront , is a newer hotel in another great location. I've found some good deals here, and other times it's very expensive. Not sure why but it would be worth checking out.
All the hotels above are in walking distance to most all the sights.
Others that are a good, but not right in the downtown area are:
Best Western Historical Inn, Best Western Spanish Quarters, Hampton Inn St. Augustine Historic District and the Historic Days Inn St. Augustine. Most of these are on the trolley line which makes them a good choice as well.
For restaurants, check out O.C. Whites Seafood & Spirits, Raintree Restaurant, Gypsy Cab Company, Harry's of St. Augustine and the Rendezvous Restaurant, which has over 160 beers from all over the world.
A fun pub type of place is the Giggling Gator, located on King Street.
Stop in Whetstone Chocolates for some really good chocolate!
I know what you mean about over planning! I'm the same way!
I think that it's part of the fun in going on a trip.
I know that you will have a great time. Not sure when you plan on being there, but the weekends get pretty crowded, but that also makes for good people watching! If there is anything else I can help out with let me know.