When I replaced the cutlass on my H28.5, I dropped the strut and took it and the shaft and prop home to work on. I knew I'd have to drill out the corroded set screws in the strut that hold the cutlass in place and that I'd have to tap new screw holes. Biggest plus for doing it this way is that you have a warm place to work and you have all your tools nearby (on most major projects, I always forget to bring something or other to the yard....).
Once the new bearing was in the strut, I simply replaced the shaft and re-bed and bolted the strut into place. While I did check the engine alignment, using the old (4) holes for mounting the strut sort of ensures you'll have the same alignment as before as long as the holes have not been damaged in the process. Hardest part of the job doing it this way is disconnecting the transmission coupler.