Depending on where you're at as far as sailing skills I would start by recommending a list of books
for you to check out, maybe take a sailing course and get yourself a bay sailor first to get some experience sailing.
my favorite sailing primer is Craft of Sail, by Jad Adkins. It is hands down one of my favorite books of all time.
My second recommendation for general sailing information is Seamanship secrets, by John Jamieson. Its a little more on the advanced side but with your engineering backround I think you'd appreciate some of the math tricks he uses for navigation
Since you mentioned living aboard
you should read The Essentials of living aboard
, by Mark Nicholas. Its a very solid, in depth
look at just about everything on that topic.
For additional reading check out anything by Lin and Larry Pardey
Armed with all that I'd recommend a 15 to 22 ft boat to start with. My first "real" sailboat was a CCB Mercury
15CB. Solid boat, very stable, easy to take out yourself, sloop
rigged with the cutest little spinnaker
ever. Plus as its a trailerable boat and far less daunting to take out than a 30+ footer you'll likely sail it more and get better at sailing faster. By the time you've got sailing figured out on something like that you'll be ready to sail something liveaboard
Once you get your liveaboard
it may be worth it to hang on to the bay sailor. It can sometimes be inconvenient to take your house with you for an afternoon sail, plus the more you sail on a regular basis the safer your floating house is whenever you do take her out.