You’ve been here awhile, and already have some good advice. Here’s what I’ll offer in case it helps at all.
I have a ‘66 TR4A overdrive that I rebuilt and installed about 8 years ago, then I installed an OD into another 4A I have just two years ago. In each case, I used a Harbor Freight transmission jack and heavy protective blankets for my floorboards and sills. My son helped with the install, but I was able to remove them myself, both times. Not that I’d refuse help for that part, too. However, back to the installation part, and assuming the great jack setup from Hamish Racing isn’t available, I think two men can line things up and get the job done.
For me, the trickiest part was knowing we had the angle correct when we tried to mate the spigot with with the rear crankshaft pilot bushing. We did use headless bolts in the engine block, but not as long as those shown above. I think longer ones might have avoided some guesswork on the angle of mating. What I do recall is that when the mating occurred it was as if something magical happened. Neither I nor my son had any idea what we suddenly did for everything to just snap together. And don’t forget, putting headless bolts into the block is also useful for removing the transmission, as it assures you’re going straight back and, as I’ve been told, can lessen the stress of the transmission spigot “hanging” on the pilot bushing.
As for process, you must of course remove just about the entire interior, seats, console, dash support, etc., and in my case the emergency brake assembly as well. You must of course support the rear of the engine with a jack (fixed if possible) and good block of wood, perhaps padded with rags, under the rear of the oil pan. Otherwise the engine will surely not remain supported by the front engine mounts. What I used under the rear of the engine was a screw type bottle jack so that if I needed to slightly adjust the engine height I could do that while at the same time adjusting the transmission height with my transmission jack.
Be sure when you support the rear of the engine you’ve done so in a way that allows room and clearance for you to maneuver the transmission and the transmission jack. And you don’t want to bump that support from under the engine.
All in all, it’s a doable job and mostly a one-man job. A few minutes of brute strength seems to do the trick. If there is one aspect of the process I wish were easier, it would be finding a way to maneuver that clutch adjusting arm on the side of the transmission so it stops constantly impeding installation and interfering with the floorboard on the driver’s side.
Other things I’d mention from experience: a) consider “machining” your tunnel cover in two ways, first with a plug hole for future access to the solenoid adjusting lever on the passenger side of the overdrive unit, and second creating an access panel to fix or replace your transmission angle drive, all without removing the entire interior of the vehicle again; b) be extremely careful to check all O/D wiring and color coding to return everything to proper connections, and triple-check the bullet connectors, especially the one off the solenoid. If that wire falls out—mine did—you’ll be removing your interior and enjoying that experience again. I also suggest you verify that the wires connecting to the O/D relay in the passenger footwell remain accessible in case you lose a connection there. Anything to avoid removing the interior; and c) consider repairing the tunnel cover wherever needed before reinstalling it. In my case I used fiberglass and cloth mesh to strengthen the tunnel and I also strengthened the bottom ridge part of the tunnel with the securing bolt holes by gluing then strips of wood along that ridge, pre-drilled to match the hole pattern. This enabled me to keep my old fiberboard OEM tunnel cover.
You mentioned tools. Here are my thoughts: When you get up under the vehicle to remove the rear cross bracket, you will want good handy open end wrenches, and I recall needing 1/2 inch and 9/16 inch short ones to reach and work easily. The other nuts and bolts are mostly accessible with ratchets, and I recall 9/16 and 11/16 on that cross member. But nothing special or dramatic. You will want to make the headless bolts we talked about for guides, and maybe even the really long ones for reinstalling, though I wonder if those might bend or be problematic (probably not). I’d definitely have a low profile hydraulic jack, probably two of them handy and ready, and small enough to not be clumsy. Plus that adjustable bottle jack was essential for me, as well as the Harbor Freight transmission jack. But let me add a note in that regard. Folks right here on this Forum warned me that the ears for the straps on the transmission jack interfere with the exhaust pipes near the transmission. They were right, and I never used the straps in any event. So, yes, I cut those clumsy ears off the transmission jack and it fit much better where I wanted it during the entire process. Here’s another “tool” for you. Good pliable comfortable protective gloves. They make a huge difference grabbing and muscling that transmission/overdrive. For me, I suddenly felt so much stronger and able to maneuver. It’s just a fact. You’ll want plenty of zip ties to move and hold wires and cables well out of your way while removing the transmission. You don’t want to damage, rip or ruin any wiring, and there will be plenty right above the transmission near the plinth.
All I can think of right now. I somehow think it’s all still a load of fun, even horsing that O/D transmission out all by myself though reinstalling is another job entirely. If you can get a helper for that last “most difficult” step, I’ll bet the rest will be easy for you.
Good luck.
PS If there’s any other detail you’re wondering about, like removing the support bracket at the rear of the transmission, or how to reattach the exhaust pipe to that funky bracket dropping from the transmission, Part 39 of the Moss Catalogue (exhaust), let us know.
PPS Since you’ll have the transmission out, will you replace the throw out bearing? The tapered pin?