92 Caprice Rebuild advice needed!!! What would you do?

I have the 92 Caprice " white whale tail" model that I have owned since 92 (dealer demo) and currently I have almost 310,000 miles on the original
tranny and engine. I have always done all my own work and the oil/filter is 3k and never more than 5k between changes. Tranny fluid has NEVER been changed and is still bright pink. Car burns no oil and you can balance a quarter on the engine while it is idling.
Here's a rundown on the car:
Everything is stock except the front end which I rebuilt a year ago and used all Moog parts. Shocks are the police package Bilsteins. I did NOT do the control arm bushings as they seemed fine.
I'd like to add a sway bar in the rear as I don't have one.
305 TBI all stock and original timing chain (going to do that puppy SOON!). Body is in excellent condition as is the interior but the drivers seat (6-way power) is showing it's age :( I'm checking into getting it stuffed with new foam as the cloth is in fine shape. It's just the innards that are sagging.
The motor runs fine but is getting tired and never had the get up and go of the 350 motor.
I am planning on a spring 2004 rebuild project and would like some advice.
Should I go with new heads, Edelbrock Manifold (the one that has all the holes for the stock emissions stuff) and a very mild cam?
Is the bottom half of this motor built for life?
The last thing I need is to do the top and have a crankshaft bearing go south on me.
OR
Should I go for a new 350 GM Crate engine Long block?
I would have the tranny done at the same time and have the shop install the engine as well because I don't think I am not equipped to remove and install an engine/tranny.
Does the 350 just plug in or am I looking at a nightmare?
I'm looking at spending less than $3k if possible.
I am looking to rebuild the car I drive daily and not a strip car but I would like a little kick added to it if possible.
Thanks for all advice because I am totally lost on this one!
psycho
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Sounds like a good play ! You get what you pay for. Obviously, your good to cars, so the investment should pay off, providing the body is good. The 350 should bolt in, and be legal. A low end cam, like an RV cam would be a good choice, as would an exhaust setup optomized for low / mid range torque.
Too much speed equipment is geared for top end , high rpm speed, you want durability / drivability, not all out speed.
Changing motor mounts, body mounts is a good move. The sway bar is a great idea ! I put them on my El Caminos.
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