It would appear that for me the easiest way would be to find a 48 -67 trans and a 48 - 53 bell housing then add a gear vendors OD and have a driveshaft made.
Besides getting and adapter from Advance Adapters can I still use my original clutch housing even if I have to have the center hole machined larger. What else is involved?
What is involved to do a T5 S 10 swap?
I doubt that is the easiest way. The Gear Vendors unit is also very expensive, not at all a good value in my opinion. A quick look on the site shows they fit various versions of the SM465 which is a 4 speed that replaced the SM420 on about 1968. They may or may not have off the shelf parts to bolt one to an SM420, and you'd probably need a 4x4 version to start with. Or make some more changes (like bellhousing bore) and fit an SM465.
All it takes is time, money, and some effort.
If you've considered the Gear Vendors then for half the money and much less trouble to install you can get the Ranger Torque Spliter that will easily work with most any SM420. You'd need to make a new shifter hole in floor/transmission cover further back, and a second one for the Ranger. Shorten driveshaft.
I don't understand what your question about the adapter from Advance and clutch housing bore are related to or about?
For the T-5 swap you can search a little on the forum. It's not really suited for the larger trucks like you have and I would not recommend it for one. I was only mentioning it to exclude it because in your research you will surly come across them as yet another a 5 speed OD option.