mshaw,
For me, I don't think U need HEI yet - all my tests so far have used the old 1960s single-point distrib, no problems yet.

You might need to use a weaker spring in place of the stronger one down below in the distrib - but first need a tach to see what your timing curve is for sure. 30 total is getting close though, if you just try 12 initial for 32 total you'd be basically "there".

As far as tired, I find that tired engines actually run FASTER if anything, just cuz they're "looser". Unless of course the valve or ring seals are giving up. Not sure if you did a compression test next but that for me is the best "tired" indicator.
Here is what I got from the 250cid that ran all the carb "shootouts" a couple years back:
135
155
142
130
145
138
I consider this a "tired" engine, not the greatest results even on compression but it still ran good and gave decent times in the shootout - after all the car ran "high 10s" (0-60mph that is!!!)

I would definitely do these steps before you tear into the engine, that way you will have a before & after. Also find out where the big Powerglide is shifting - mine was shifting about 4500 or so, probably a little lower than the 4bbl wanted but I didn't want to abuse it so left it there - I was looking for improvements and comparisons, not the last tenth by revving the old six higher.

Thanks for all the photos you are posting it makes for some interesting threads!