Having driven a 302, 5.0 and 5.8 in the same basic EB, I'd take the 5.8 over the other two and say it's WAY more fun, etc... If I had $1000 or so to spend, I'd try and get $600 or so for the 5.0 and sink that into the 5.8.
The later model 5.8s are roller cam equipped, and that makes them rev quicker like the 5.0s, a few more HP due to the lower frictional losses and there's not a lot of difference price-wise.
I can buy a '94-97 5.8 for $750 or so, add the Fox swap 'Stang pan for $150 and a low profile intake (to get it under the hood) $300-600 and you've got a lot more engine and it's going to make you smile!
Personally, I'd never stroke a 5.0 vs. swapping in a 5.8 UNLESS class rules required it. Bigger mains and bearings in the 5.8, etc... Then, when you're bored of it in a couple of years a $350 crank and you're at 396 CI. Same truck rods, no block clearancing, etc...
An AOD is like a C-6, a HP drain. The 5.8 won't care, the 5.0 feels it.
Joe