Re: Rubber boot under outdrive?
If you don't have a service history on the boat (and I mean from maintenance and/or parts receipts- not 'the owner's word') then you should plan to pull the drive, inspect gimbal and u-joints, and replace all the bellows.
If the the exhaust bellows looks good and the boat is water-tight it probably isn't an emergency, but should be taken care of in the near future. I bought my boat from a dealer, and it was in the water when I took posession of it last Spring. It had gone through an external visual inspection by the surveyor, and was sea-trialed (no noise, loose steering or any other bad indications), so I decided to just run it for the season.
As soon as I took it out of the water, however, it was gone over with a fine-toothed comb and got a major 'tuneup'. The shop owner questioned me about any shifting issues (none), then they lubed it, replaced the bellows and a water intake tube, all the zincs, pressure tested the drive, inspected it all for signs of corrosion, then pronounced it 'good to go.' It was worth the money ($600) to give me that peace of mind and establish a baseline for future maintenance.
My .02