Welcome to 3FC. We are kinda neighbors and I am 33 too.
With the achilles heal, I would suggest trying to warm up just a bit first, do some good stretches before you start to really work out and then make sure to stretch again afterwards. Otherwise, have you seen your doctor about it? Maybe there is something s/he could recommend to help.
Weirdly enough, I am actually finding I like exercise. After so many years of hating it, I am still surprised by this. I enjoy several different things. So far, I don't like the idea of anything that involves other people because I want to go at my own pace. I belong to a gym and really like the elliptical. It was tough at first, but I actually find it easier on me than the treadmill (which I also like). I also really like lifting weights - it makes me feel strong. I like taking walks outside when the weather is nice and when I get fitter I really want to take some form of martial art or fencing (or both) but I don't feel quite ready for that yet.
I have several videos I like to do as well. Angie just mentioned one of them on the main thread (where you are welcome to join into) - Just My Size yoga. I also really like a the Woman Power Workout from Fat Chance Belly Dance, but it is pretty long so I don't end up doing it that often. I like the bellydance videos by Veena and Neena - they are a lot of fun and pretty low key. A lot of people like Walk Away the Pounds (WATP) - it is a good place to start. Leslie Sansone ends up annoying me if I get too much of her. Actually one of my favorite things to do is just watch tv and do WATP type walking.