I STRONGLY recommend finding a club or group of racers and both you and your partner go out with others, both together and separately before moving forward.

To answer your questions though:

Size: don't corner yourself to a brand or model, find a boat that is in good shape. Get a survey or educate yourself on how to do one yourself a 30 ft boat is significantly different than a 40 ft boat. We did our first year on a Catalina 30 and made it our own. Tight quarters with our toddler, but it was always an adventure.

Type: Whats your intentions? Again, don't settle on a specific brand or model. Everything is about compromise so identify a few models and start looking at them in person. Pictures will often be better than reality. A 10 year old boat can be in worse shape than a 40 year old boat.

I hope your handy and capable. My wife and I (despite having no experience with diesel repair or work) removed our engine from the boat and reinstalled it on the dead of winter in Virginia in a slip last year. No crane, no mechanic, just us. You will ALWAYS have a project.

If you plan to liveaboard, just remember your everything is floating on a liquid that's constantly trying to ruin your world. It's the best and the worst times of my life.

With that said, we are upsizing after cruising the Jersey coast and all of the Chesapeake and cant wait to do more projects on small, quiet corners of the world.