I never had any experience with Avgas damaging any rubber parts. I have ran it several times in my 302, and my dad has put it several times in his 56 thunderbird with the stock 312 and never had a problem, and they actually ran better. I tried Unicals 76's 104 octane racing fuel before, and I didnt notice any difference at all compared to 87.
Keep in mind, aircraft engines dont have high compression ration either. Some of them are as low as 8-8.5 - and these are normally aspirated. I cant recall any off the top of my head that are significantly higher.
The lead was added to help keep things cool and at the same time it increased the octane.
Lead can foul plugs if the engine is ran at low speeds for extended periods of time. Aircraft engine manufactures recommend to run the engine off idle just prior to shutting off an engine to remove any lead that may have accumulated.
100 LL specific weight is different from racing gas and you may possible have to rejet the carb, although I didnt.
100LL is also a more refined and cleaner gas.
But as stated earlier, if you dont have the compression then it wont benefit you much. Higher octane fuels do not have higher heat value thus will not produce more power.
Avgas does make the exhaust smell really sweat though. Not that I sit there and sniff it, just something Ive noticed.