cutlass bearing first or last?

I'm finally getting around to putting the engines back in my boat and I'm phasing the tasks. I feel I should put the engines and transmissions in first, align everything then replace the cutlass bearings. Since I only have the weekends to work on the boat, I am identifying things that I can hire out and work in parallel. Is this something I can have done independently of the critical path or should I wait until the engines are in and aligned to the old shaft position? I have removed and replaced the engine stringers so nothing is really as it started (hopefully fairly close )

 

I'm not an expert on this, but here's what I'd suggest:

Installing the engines and transmissions first should be fine. But I'd replace the cutless bearings, and whatever other shaft supports are being reworked, before doing the final alignment. Then you're aligning the engines to the actual position of the shaft in the new configuration. (The coupler doesn't care what things were like last year, or what the drawings say things should be like. It only cares that it's properly mated to the shaft it'll actually be turning.)