No, I insist you try to machine it for a throout bearing. 
(I just want to see what happens!
)
Hee hee… Yah, pilot bushing. You’re exactly right on the throwout description. Hey, I had about four free minutes to surf… 
Yes, I think the bellhousing will be the sticker. Only Cadillac never had some form of manual tranny behind the musclecar-era non-Chevy GM big-blocks. A bellhousing from/for a Pontiac, Oldsmobile or Buick (in all cases either big OR small-block, they’re all the same) will fit.
Barring that, since of the three, none were real prolific manual-tranny users, and in all cases you’ll end up with an aluminum housing, you can ring up your local race shop and ask around for a bellghousing/scattershield. It’ll be steel, probably a near-universal fit, and about $300 and up.
Any decent tranny should work, 'cept maybe the generic Saginaw 3-speeds. A T-10 (or Super T-10) would be nice if you can find one, any of the Muncies, or heck, jump for a newer unit from NV and get an overdrive 4-speed.
As for Advance Adapters, they make damn near any adapter you need- Jeep tranny to Chevy truck transfer case, Ford tranny to Jeep transfer case, Toyota to Jeep, Toyota to Chevy, Chevy to Toyota… heck, there’s even Toyota-to-Toyota-to-Toyota, if you like having 235:1 low-range for your four-by. 
You need a bellhousing though, not necessarily an adapter. Yes, they make bellhousing adapters, but to be honest, I don’t recommend them.
Scylla- Trust me on this: The clutch linkage will be FAR harder than you expect. The tranny and clutch, with the right parts, will be essentially a bolt-on. But the linkage will require at least some modification, and unless you plan on stripping the entire dash to a bare framework, it’ll be nasty, cramped work. AND, (I have a little experience here) if you DO do it with a stripped dash, you may guarantee that you’ll discover something kind of important, like say the speedomoter cable, or the left side of the guage cluster itself, won’t fit with the new bracketry in place.
Measure twice, lay it all out, go have coffe and think about it. Come back, measure three more times, consult an experienced professional, measure two more times, THEN cut.