It is going to be much easier to change the crank out of the engine if you remove it and put it on an engine stand. It is possible to do it in the car but with the amount of disassembly necessary, it is going to take a thousand times longer to do then just pulling it out and doing it the sane way.
For one thing, engine oil is going to be constantly dripping on your face and the bigger issue is that in order to drop the crank down, you need to disconnect the transmission from it.
Additionally, you are going to need to know the amount of thickness you need added to the bearing. To do that you need to pry the crank to measure the clearance that you have. Better to do that on the stand. I see it as likely you are going to need a custom thickness bearing and here's the issue, you can't know if for some reason, the thrust face of the crank is worn unevenly?
But even determining that, it is doing the entire thing backwards. Those bearings are likely to be made in some kind of standard oversizes which means that the crank is the thing that gets refinished, even on the thrust face.
Frankly, I think that it is all better to pull the engine and count on replacing the crankshaft.
Crank refinishers here only get like $150 on an exchange basis. If everything is stock, you won't even need to have the assembly rebalanced. Just change it out with new bearings that likely will be undersized.
In my racing days, no one wanted to use a crank with more then .020 over sized bearings. (If the crank is undersized then the bearing is oversized)
Correctly or incorrectly, the feeling was that because there was more metal in the bearings themselves, they were thicker, that it gave more possibility of essentially "squashing" the bearing. It is important to remember though that those engines were being turned at excessive rpm's so normally a .030 under crank with .030 over bearings, would never be an issue in street car. In a race engine, it might be.
I personally never saw that happen but who knows for sure? Maybe just racers paranoia?
I think that in the case of a Cleveland, fully grooved main bearings is an excellent precaution to build into the engine.