Electrical problems

[Squareforceone]

Okay so I have an 84 c10 that i pulled the 305 out of and put in a 350 with headers ever since then it's had a problem starting when it's hot. So i put a heat shield on the starter to see if the headers were heat soaking the starter and it had no change. So i bumped down the initial timing to next to nothing and still had no change.. The 350 wasn't built by me and was giving me head aches so I pulled it out to rebuild and put in a different 305. Well the 305 is stock minus headers and intake/holley carb. Still having the hot start issue. But now on top of that the truck randomly won't charge. Took it on a few drives were things were fine others where the battery started going dead while driving. One of these times I brought it home and put my fluke on the battery and it read 9v while charging (know good alternator) Then today I started it put the volt meter back on and it read 14v running. I'm assuming I have a bad wire rubbing somewhere?? I've cleaned up all the grounds but still have had the issue. Where all should I check? Thank you.