I understand where you are coming from. I have a 1999 2 door that I bought new. Sold it a few years ago, but kept in touch with the buyer, and just bought it back.
I also have a nice 1996 Bronco with mild lift etc, so not sure what I want to do with the Tahoe now. But doing a lot of research.
I also know Jonathan Ward - not personally, but have spoken with him in length on the phone. My wife has met him and done a tour of his shop etc back in April. We have contemplated one of his broncos. BTW, He has also done a few killer K5 blazers - one of which is back on the market now. He is top of the line. If he were to take your tahoe and restore/mod it, I bet it would cost 250k. Maybe 200k if you didn't go too far. Last I heard he was 18 months out.
For an engine, mine has 170k on it, if it ever needs replacing, I would probably do the HT383. I think it is a direct replacement.
5 speed manual would be fun, but no idea what a nightmare that swap would be.
Paint, suspension, lift, wheels, tires are all fairly straight forward. I think any reputable shop could do a fine job if you figure out what you want.
What do you want it to look like? Stock, original, mildly upgraded/udated? big lift etc.