Which outdrive do you have?
Either way, it’s possible, just a real pain getting to the bolt that holds the retainer plate on.
Personally, Ive done it both ways on Bravo II’s and will remove the drive and gimbal ring in the future. The special tool for the gimbal pins can be bought on eBay fairly cheap.
Primary reason is being sure that the sealing plug/gasket is seated properly and the bolt torqued well. My boat is in the water all year round and I didn’t want any potential leaks given this thru hole is right at the waterline.