I've owned my car now for 10 years, and in all the time that I've owned it I've NEVER been this frustrated with it. Here's my problem:
About two months ago I replaced my old engine with a new one. The specs for the new engine are as follows: stock 440 block (.055” over), stock forged crank, no-name aftermarket H-beam rods (w/ 7/16” bolts), KB forged pistons, Indy SR OOTB (gasket port), Indy 2D Intake, 850 cfm Holley DP, 440 Source roller rockers, TTI 2 1/8” headers & 3" exhaust, Pro Comp dist., 7 qt. pan, .520”/.550” lift, 242/252 (.050”) and 310/320 duration hydraulic flat-tappet cam. The compression ratio is about 11.5:1 and I run a race gas mixture.
The top end of my old engine was the same (except for the cam) and I used the same 440 Source starter and B&M converter (3200 stall) that I had with my old set-up. While I was moving the distributor from one engine to the next, I noticed that the rotor needed to be replaced and that the anode coming from the coil was missing (I guess the spring that was behind it had been serving as the new anode for a while). I replaced the cap and rotor and also bought 4 straight high-heat boots for the 4 cylinders at the rear of the engine that were near the headers.

Everything seemed fine until one day, while trying to get the timing in, my starter sheered off a half dozen teeth from my ring gear on my converter (it's a 727 car). I dropped the transmission, sent the converter away to have a new gear welded on and put it back in. I fired up the engine and - TA-DAH! - off come a dozen teeth. Rinse, repeat.
So now I'm on new ring gear #2 and I retarded the timing and this seemed to fix the problem (I'm at about 16 degrees initial). Yesterday I went into the garage to start it up, and when it fired I could hear that it was back-firing. I checked to make sure that all of the plug wires were good, and I fired it up again, only to hear the all-too-familiar sound of a tooth being sheered (why isn't the starter bendix softer than the gear teeth?). This time I was lucky: only a half a tooth is missing and I figure that I can take it to a welder and have them fix it without having to remove my transmission. Obviously, I'm scared to try and find the problem through trial-and-error at this point because I don't want to lose any more teeth in the process.
The problem is definitely in the ignition somewhere (and yes - I checked the firing order).
Has anyone ever had anything like this happen?
This is really frustrating and I appreciate any help that you can give!

If I don't get this thing figured out soon, you may be seeing a '68 Roadrunner on the "For Sale" board.