I'd say "no" to a 305 head on a 350, every one of these motors I've seen tended to run hot, ping under load, require 93 octane no matter what and the smaller 305 valves would cause them to have excellent bottom end and then promptly fall flat on their face about 4000 rpm.
My choice would be to find a 96-99 5.7 Vortec in good condition from a running truck/burb/Tahoe/Yukon/van along with the pcm for it. make sure it has good oil pressure. While you have it out, definitely change the head and intake gaskets-these are notorious for having problems over the long haul, but fel-pro makes a better design that gm started using as a replacement years ago. Use the injectors from the 5.7, or if you have the cash, swap to the 2000& newer 5.7 vortec spider assembly found in vans, it's much more reliable. exhaust manifolds and sensors should be a bolt up. the wiring harness should be plug and play, the only thing i'm unsure of is if the pcm will set a fault code going to a manual trans, you may need to have the pcm programmed around this, there were no 1500's that came with a 5.7 and 5 speed. overall, it should be relatively inexpensive and gain close to 40 hp and 50ft/lbs of torque. be careful of future mods, as the 5 spds will break from excessive torque if you get too happy on the skinny pedal with a 5.7