The basic TF727 and 8.75" rear end you very likely have can hold a lot of power if in decent shape. If the transmission is a high mileage original a moderate performance rebuild may be in order. Otherwise should be good to 400-500 HP. The rear end should be fine with any engine and street tires. If you start running drag slicks and pushing 500-600 HP with hard launches, the rear could become an issue.

You have lots of choices. You can warm up the 383. It is kinda a tough engine to build for performance due to short stroke and low compression but can be done.

Much better results can be obtained by stroking and increasing displacement. There are lots of well proven streetable combinations up to around 500 cubic inches. With cam, compression and carburation chosen for street use they can be easy to drive and reliable.

A nicely built engine would use a quench style head and piston combination to allow good compression on pump gas. Also a moderate cam. Starting with a 383 block, around 438 cubic inches with 3.75" 440 stroke, around 440 or 450 cubic inches with 3.9 stroke on up to around 500 cubic inches with 4.25" stroke. Or you could change to a 400 or 440 block if readily available... though I do not think that is necessary with your goals.

The stroker option does best with aluminum heads... 440 source stealth, Edelbrock RPM or Trick Flow. Also does best with careful blue printed rebuild to dial in piston height, quench and compression.

It really comes down to how far you want to go and resources available.