I just went through the same agonizing decision.
I had my distributor ring gear teeth sheared off, I replaced it, two cyl valve giudes were worn, causing fouled plugs that needed to be changed once a week(these are AC Delco plugs $20each), 1l of oil consumed a week, tick tick tick in the morning, etc.
My dealership even offered to let me go to the auction as a driver for thier company and I could pick out any truck I wanted and just pay $100 over auction price. A good deal!
I agonized over selling my rig, or rebuilding/replacing the motor, etc for over a month. Hmm'd and Haw'd.
Finally our old guy mech and my dad both told me that's it's better to keep the devil that you know vs the devil that you don't know. I figured the old cats who are almost double my age probably have been around the block once or twice and knew what they where talking about, So I pulled the trigger and bought a new GM crate motor.
I've never regretted that decision.
BTW, a factor that possibly swayed my decision to buy a new motor vs rebuilt heads was the thought of that many chunks of metal from the sheared gear teeth running around in the block. I was scared of that. That's a lot of missing metal parts.