355 vs. 383
3.48 to 3.75 = 0.27" per stroke = 0.54" per rotation
0.54" X 1000 rpm's = 540" = 45' per minute
100000 miles on a car with 3.23 gears, and .70 overdrive
100000 X 3.23 = 323000 X .70 = 226100 rotations
355ci 226100 rotations X (3.48X2) = 1573656" = 131138' = 24.84 miles of piston travel
383ci 226100 rotations X (3.75X2) = 1695750" = 141312' = 26.76 miles of piston travel
so in theory a 383 would have 1.0775 times the wear of a 355
but then again how many of us are building them to go for the long road, not me

IF 60 mph in OD was 2000 rpm and you drove the whole 100K in OD, the engine would turn over about 200 million revs. Remember it's about 2000 revs per mile in OD, not 2 revs per mile. Because we don't cruise always in OD, 100K is more like 300-350 million revs or about 30,000+ miles of piston travel.
My LT1 has over 106K on it now and it still uses virtually no oil (Mobil 1 since the first change). I'm always impressed with the durability built into modern engines.
383 vs. 350 really isn't about engine wear, IMO. I suspect that a built 355 or 383 will suffer a lot more from being "exercised" than will a unbuilt one. If you have it, use it!
My $.02

I went with a 380 LT1. In the end I spent a lot of extra money and research to get the heads to flow enough to feed the extra 30 cubic inch's. CFM numbers mean nothing. It is all about port design
The Best V8 Stories One Small Block at Time
If you get a new crank go ahead and get a 3.500 in stroke. Puts most pistons closer to the deck so you do not have to cut it as much
You only get a few extra inch's but I like having all the deck I can get 
If you were looking for a 383 kit we have one laying here
and a 4 bolt Splayed main block, she is a virgin bore and deck
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