It all depends on how comfortable you are with tearing things down. I had never even opened a transmission in my life when I took on my project. However, I had done a fair bit of wrenching, including rebuilding an engine and I am an engineer.
All that said, I started with three transmissions - TR6 non O/D, TR4 non O/D and TR3 O/D (but did not work). In the end I took the guts (all of them) from the TR3 transmission and the broken TR3 O/D and put those guts in the TR4 box and added the J type overdrive to the back of it. Before I actually added the O/D to the box I built a test jig to figure out what was wrong with the O/D on the bench.
In the end I got a 3 syncro O/D box working and in my TR4. And with never having done any tranny work in my life (other then removing and replacing clutches). So you can do it if you have the motivation. I spread the work over a few days as I got advice from this forum as things cam up (I could not have done it without you folks) and I had to go buy one part.
Before anyone asks, the reason I went with the 3 sychro guts and not the 4 was that I only had the O/D main shaft for the 3. Some day I will buy a 4 main shaft and put the 4 guts in there (and that too tells you how "simple" I ofund the whole thing to do).