Low hanging to me is and leaking gaskets, core plugs, or the like if they need it.
Compression test you do with the engine warmed up, all plugs out and WOT on the carb. Leave the distributor plug alone and just disconnect the coil wire that goes to the cap. Probably can leave the fuel alone, the floats and seats will keep the bowls from filling as you turn it over 4-6 times. Write down the results and post. Honestly with 30k and it runs good I would leave it alone.
Changing things can become a slippery slope like converter size and adequate springs for a cam change and are the push rods correct length still. Heads can change compression ratio, which means you may need to change cams or degree the one you have to set the dynamic compression ratio and are your rocker providing the correct geometry on the valve tip and enter push rod length again. Now is you intake and carb up to the task of changes? I know it sounds daunting but It can and is done, just know what your getting into with a change.
Then when you have a hot motor can the car handle it? Brakes, suspension, etc all pivotal to change and it is a package.
If it were me with what you have I would fix the leaks, review the current tune and see if it needs help and drive it. If I wanted more power i would find another core 360 or 5.9 (or buy a crate engine because building an engine isn't cheap anymore) and build a new engine and plan when supporting parts it need to be successful.
