Ford 223 I-6 HELP!

[Brady]

I have a 1960 F100 with a 223 inline 6 that has given me problems for a year.

-I had the engine rebuilt a year ago.
-It has a Clifford intake and headers and Weber 2 barrel carb.
-I have installed a new distributor and cap.
-The carb has an electric choke
-It has an electric fuel pump which then runs into a weber fuel regulator. (to achieve the required 2.5psi max)

It started and ran okay a month ago until the choke disengaged then the engine would die.
I bought a jet kit and upped the idle jet one size (from 45 to 50)
At this point I realized that gas had made it into the oil (all over the intake too.) Alot of gas! About 5qts. I pulled the carb apart and found the float stuck and not properly adjusted. The accelerator pump diaphram had deteriorated so I replaced that (this is a new carb) The oil and filter were changed.

I had problems with not being able to keep the fuel psi below 5. I had plumbed the regulator backwards and was able to achieve 2.5psi once I reversed it.

Okay, done with the back story...

2 weeks ago it fired up and was running very smooth but had a hesitation on acceleration. So, I bumped the timing back just a hair. I tried accelerating again and it started running very rough and died. I haven't been able to get it to start again. Changed the plugs and moved the timing back to the original position. Changed back to the smaller jets. No change. It cranks and one cylinder might try to fire and it back fired a couple times. Its getting spark and clean fuel.

Could I have jumped a tooth on the timing chain?
Any ideas or help would be greatly appreciated I am at wits end with this thing.

Thanks in advance for any help!