New to the A body scene, school me!

I am thinking more along the lines of a pro touring feel. I want her to run like she's on rails, have you guys heard anything good about the hotchkis tvs system? As for motor I would eventually want to move up to a 340. As for now and funds allow probably bolt on stuff like manifold, mad excetra.

Below is the way I'd go. Skip the 340 and still make the same HP at a lower rpm with more torque to boot. Though I don't think I'd stick with the 273 over the long run.
The roller 360/904 combo is an excellent one. 400HP from a roller 360 is easy and very streetable. An 8-1/4 rear is more than capable of handling this power level. It will also save you a lot over a 8-3/4.

I do not know what Hotch has for your car but the do make very good stuff.

Do your suspension setup first. Then acquire the motor you want to use, take a real hard look at the late 80s/early 90s LA 360 Roller Block, pretty much the top dog of production LA blocks. That roller cam setup is a big advantage over standard flat tappet blocks.
Personally I'd just keep the 273 running (maybe swap on a 4 bbl intake and carb and that's it) because you want to swap out to a bigger motor later anyway. More money to build the bigger motor is always a plus.