Doesn't Wilcap already have an adapter for this?
The application, not the year, determines the shifter position. You want an S10 T5 with the most forward shifter location. Early late has more to do with gear ratios (normally) and speedo type (electronic vs cable), but the very last S10 T5 use the Ford front (bolt pattern & input shaft).
Typically, the mechanical speedos were used through '88. '89-90 were transition years - I've seen both electronic & mechanical (mostly electronic).
Some T-birds also had a mid-shifter.
I think that's in the eye of the beholder. I think if you're looking for off-the-shelf-easy, the Camaro T5 is the easiest to get bolted up, but you need to swap the S10 tailshaft for most hot-rod applications. The S10 uses a slightly longer input shaft than the standard Chevy/GM bellhousing the majority of adapters are made for. This has been addressed in various ways and tolerances being what they are, sometimes it just works. The Ford is challenging.
W/O modifying your center X-member? Not likely. But everything else you've asked for is do-able.
MAC Speed in Australia or New Zealand are making them. Adapting to the 8BA stamped steel bellhousing is supposedly pretty easy, but I've never done that one. I need to look into it more.
This is why I like the stamped steel bellhousing to try this swap - redrill one hole and weld an ear on the bellhousing for the last hole...at least that's what I've been told. Again, I've never done it.
I wouldn't think they're any deeper - didn't they use all the same basic trans? That would preclude using a different bellhousing...