Hi John,
It's not too bad with two people. Since there was only one of me, old & weak at that, I did it the hard way. I have a roll around lifter but unlike yours, the wheels are too high to let it go under the Healey, so I used a ceiling mounted "chain tugger." The roll around is still handy for other uses. Yours apparently has very low wheels.
Transmission removal --- See pics --
1- Support the back of the engine on a floor jack with it's rollers fore & aft.
2- Remove seats & all interior obstacles. I even removed the steering wheel before it went back in.
3- Placed a temporary drop center cross member (3/8" by 2" by long enough to span the frame members under the front of the transmission, for temporary support.
4- Unbolt the transmission, remove drive shaft etc.
5- Slide the transmission back & rotate it to clear the firewall opening. The U support holds up the front.
6- Slide the transmission back far enough to turn it sideways.
6- Attach a lifting sling to it.
7- Raise it high enough to clear the car. In this case I couldn't lift it high enough to clear the windshield & didn't have enough room to roll the car forward, so I removed the windshield & rolled the car back & out from under the transmission. (8 1/2 ft. ceiling.)
8- Changed hoists & rolled the hoist & transmission over to the work table & lowered it onto the table.
9- Installation is the reverse!!!
In retrospect, couple of comments. Starting with the back end of the car into the stall first, it wouldn't have needed to be lifted so high & the windshield could have stayed on.
When removing the engine There was the same lack of lifting height problem. The engine wouldn't clear the front shroud. I had to remove the front wheels, lower the floor jack, & use it to roll the car back & out from under the engine.
The "Oberg" tilt lifter takes up more lift height than necessary & a simple chain attached to the engine or transmission is adequate. The "Oberg" is now in the unused junk corner.
It could have been easier, & most folks would have less trouble.
Some years ago I pulled & replaced a Chrysler Hemi with transmission attached using the same setup & had no trouble at all.
To move the engine, transmission, around the shop I set it on an old "Champion Spark Plug" creeper of the wooden oak variety. These things will take a tremendous amount of weight. I even moved the Hemi around with it. Also, moved a 13" X 40" metal lathe on two of these creepers.
I think this covers the "high points".
D