Well my 305 is getting a little "tired" and I think the winter may have gotten the better of some of the seals in it....regardless. I have searched etc...and understand what needs to be done for a 305 to 350 swap including tuning..but regardless I want to get peoples opinions

A relatively mild 350 such as:

290HP / 350 Long Block Pre-Emissions GM Crate Engine :: 12499529 - SDPC

If I go with something like the above a stock Caprice .bin would be good enough to get me driving, and have a bit of fun? It is not a daily driver, but regardless I want it to be reliable and not have it sit for months after I drop it in.

My Primary concern is getting the car running, and running "ok" enough that I can then "tweak" it down the road as I learn the prom burning details etc do you think that would be ok with the stock caprice l05 or cop car .bin as a starting point?

Suggestions?

What ECM are you planning on running. Because if it is a caprice computer then yes, use the stock caprice configuration and datalog and see how your fuel/spark is acting and adjust accordingly.

Sorry...would plan on using the stock ecm (89 with an L03...cant remember the ecm #) and then burn a new chip with the caprice/cop car .bin.

You need a better fuelpump and set the fuel pressure.
The orginal fuelpump can only support 15 psi and max 260 hp with 61 lb/hr.
With 290 hp you need 20 psi with 61 lb/hr or 25 psi with 55 lb/hr.
Go for a stock 350 bin and set the bpw for it.