If you just want a reliable driver it is easiest to do it with the Olds 350. IIRC, Olds used high nickel blocks which GM did not use in Chevy engines. For a transmission, use a TH 200 4R. It fits anything GM, and can be made reliable. Plus the gear ratios are far better than the Th 700 R4. Run a modest gear like (my favorite right now) a 3.23, a Quadrajet and an HEI and you will have plenty of trouble free motoring. The Chevy has advantages when it comes to price, parts availability and workable native EFI setups. It also has a very good oiling system and may be available with a high nickel block too (research is needed to find an application). The cam that comes stock is irrelevant as it will be changed (and only 305's had that issue). However, it is more work to properly swap in the Chevy than the bigger Olds family swap. At the mild level you seem to be wanting to go with, there is no real advantage to the Chevy.
Now if you want to start from scratch, go with an LSX. I would try to use a smaller engine like the 4.9 or 5.3 out of a truck instead of the larger ones for your application. Why? Iron block, and better fuel economy on the highway due to a smaller displacement. Run the ignition off an MSD box (special one just for an LS), and run the injection off a Megasquirt. This will let you bypass a lot of tricky things like CAN, OBD II, and Passkey. It will also bolt to a standard SBC bell housing, so I would again go with a TH 200 4R if you want an automatic.
All this supposes that an emissions inspection is not in your future. If you do have to pass smog, go with the Olds 350 and run it off the CCC computer that is native to your car. Paint it black, use the 307 valve covers and use an intake with an EGR valve provision from an aftermarket company but grind off the brand name of the maker before sand blasting the intake. Richen the secondary metering rods, and consider a custom made PROM chip burned in an emulator to set a better timing curve. I would also cut off the thick stop on the secondary air valve to make the carb a computer Quadrajet 750 instead of the 600 it is. For exhaust, run a single 3 or 3.5 in cat with a Hooker cat back system and the stock 350 exhaust AIR manifolds extrude honed internally and run with a good free flowing Y pipe. Get a 80's 442 air cleaner base too, while you are at it. Get a cam with a wide LSA, and run around 9.5:1 compression for good idle quality and decreased Hydrocarbon emissions. Will this ensure a pass come smog time? No, but it makes it more likely.
As far as practical goes, that is exactly how my car was planned. It was initially supposed to be a pizza delivery car ( and was for a year, or 40k miles) and as such fuel economy was a big concern. Mine is Chevy powered, but it was originally a Buick V6 car and I had lots of Chevy stuff and knowledge, so I went with it. It was also built in the 90's when information about stuff other than Chevy was hard to come by and the internet was in it's infancy (and not in my home). So, how did it do on gas? initially, not well. I was getting 12 mpg city and it ran so rich that it belched black smoke. It was an issue I only solved after taking the car out of service and traced back to an AIR system leak that tricked the O2 sensor into seeing dead lean instead of the right mixture. As it sits now, it gets better city fuel economy than the V6 did by about 1-3 MPG (The V6 got 14 mpg city, 29 highway). It is worse on the highway though by 5-8 MPG. That is normal though as a larger engine needs a larger minimum amount of fuel to run at a steady state speed than a smaller one of equivalent design efficiency. Surprisingly, the switch from 2.41 gears to 3.23 netted a huge gain in fuel economy because it keep this engine in the power band. Even still, I have a compound 4th of 2.14:1, which is lower than the V6's 2.41 compound 3rd, so the engine RPM for equivalent speed is lower with the v8 than the V6 at a steady state speed. I could write a book on theory here, but I will stop. Let me know if you want to know my whole combination and I will post it here.