hot start issues

[primrrd]

81 305 automatic.
- mostly stock with emissions removed, rv style cam and edelbrock performer intake and edelbrock carb, dual exhaust on stock manifolds.
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I'm due for a tune up, but in general, if I start it every day it jumps to life in a second, I have to pump it and get a 4 or 5 revolutions with the starter to get fuel to it if it has sat unstarted for a few days. My problem is when I drive it and get it up to temp (no overheat, or hot run issues at all ) it HAS to cool down, or it is very hard to start. It seems like both the starter is dragging when hot and fuel to the carb is an issue. Battery is new. I have never changed the starter and ive had the truck for over 8 years. Just recently seeing this as an issue.. though when I think of it, the truck has always been harder to start when fully heated up, or after a long drive.
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Any ideas? Is the starter just on its last leg? should I heat shield it?
I could just throw a new starter on it and see, but trying to get an understanding of what I got going on.. and I'm not crazy about putting an autozone starter in it either.. Is there a "high torque" or later model starter for a gen 1 chev smallblock that is mo better?
Seems like I gots 2 problems.