Man, with stuff like this, I could write a lot soo I'll try to keep it short.
How low is your idle? Is the timing set properly? Are you running factory dash pot? Do smallports even run a dashpot?
Aside from the obvious, When it doesn't start next, can you pull the return line off the rail and see if it has fuel? Then test the spark with a spark tester, not just confirming spark with a spark plug jammed into the lead earthing on the block. Having spark doesn't mean it's enough to start the engine, it has to be strong.
If the obvious spark and fuel are there then disconnect all the unnecessary sensors around the engine. I doubt it's the problem but it might tell you something.
The other thing is it might be (and probably is) the distributor. Try swapping another distributor in there.
Last and most annoying thing is the wiring loom. When the car's running all good, shove the loom around in various places and see if it causes any of the problems you have.
That should keep you busy for a while.
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