I had your same situation with my small block. It ran great at 42 degrees with good street performance. Total advance was well over 50. BUT I worked my way back to near-stock timing with quick centrifugal advance (yellow springs), early secondary (white spring) and short (14 degree) vacuum can. Although it ran great at 42, it is a real rocket now at 18. Both setups run very cool, in fact I don't use my electric fan unless I'm stuck in traffic. No starter drag either.
At 42 it was running silver advance springs, plain secondary spring, and 20 degree can. If you have a mild cam like I do (Comp 252), get your advance all in by 1800 and your secondaries a tiny bit later. This is for a tall rear end! I have a 3.00 Ford, if yours is higher, this may not apply.
Work your way back to near stock. Just because it runs OK highly advanced doesn't mean that's the best setup. Your carb may be a little big for a mild small block, so your secondaries may be coming in late, if at all. If hot starts are a problem, something is wrong. It should fire instantly.