I'm 5'10" and can fit on a WSD or a men's bike. Most important thing to any bike is that it fits right. If your Trek bike fits you can do what you want.

It also depends on what kind of riding you plan to do..street or mountain. You might like a 29er MTB (tires that are 29 inches instead of 26) if you are looking into a mountain bike. 26 MTB are almost too small for me. Check your LBS if you are wanting a new bike or needing to see if your bike fits.

Some great books that I've picked up are "Bicycling Bliss" by Portia H. Masterson, "New Cyclist Handbook", "Bike For Life", "Serious Cycling" and a mountain bike book I have on my Kindle, but can't find to give you the title.

Crashing is part of learning. Last crash was a couple of days ago while going up a steep hill, tried to change to a lower gear and the chain came off as I was going too slow. Ended up on the side of the road. Sigh. I still have a giant bruise from trying to do a wheelie on my MTB in my back yard 3 weeks ago. I can at least get my front tire up more than a couple of inches now. Grass is the best place to fall but stay off of busy roads if falling is a concern.

You'd have to check your LBS for any kind of classes. If you have local bike trails, go out for rides. Most people are very kind if you fall off. Let the mean people laugh..their turn will come. The important part is that you are having fun. Make sure you have a helmet. It has saved my head many times this summer.