Got my '78 Cutlass.. stock 305. th350 trans. Stock rear.. Not sure of ratio, but it's probably a 2.41 peg leg..

The motor runs good for the most part. It's all original. Not sure of exact mileage.. But it's over 100k. Smokes a little bit on start-up.. Needs either valve seals or guides.. But it's not that bad. Hard to say if it burns oil b/c it leaks at the pan gasket/rear seal..

Trying to decide if I should focus on the motor.. I would like to leave the original 305, just have it rebuilt. Yeah, I know. 350...etc.. I've had a 406sbc and I know the power potential I am giving up.. Not that direction I want for this car.. When I do the motor, just .030 over, flat tops, vortec heads, intake,headers,mild cam... Nice cruiser motor..

Or.. leave the motor for now, just maybe do the heads.. I have an edelbrock intake I could throw on.. and I have shorty headers.. But I'm in no rush to do the headers b/c then I gotta replace the Y-pipe..
And do swap out the rear end.. I found a 3.73 non-posi local.. For $100. Or a 3.55 posi ( I think its an 8.5) for $400.

I don't take this car on the highway that much.. If I do, it's within a 10-15 mile trip.. But eventually I wanna do a 200-4r trans too.

So, Motor.. leave trans.. Leave rear..
Or Minor touches to motor, do rear.. ?

 

I, personally, would do as little as possible. I like to make things last as long as I can, within reason. If I was worried something was going to go soon, I'd hunt out a cheap parts car for $300-$500 that has a bunch of what I want. I'd strip it, or just hide it away until needed.
On the other hand, I've spent thousands of dollars on a car, and then sold it at a huge loss when I was tired of it, so how rich do you feel?
This is the fun part, you still have your money !!

 

The 3:55 would give you the best 'bang for the buck' at this point.