My only comment would be that if it got real bad or tore all together that is a BIG hole directly into the boat. I would fix it. I've read people on here do it without even pulling the bellhousing, just pop out the cable. I did mine when I had everything off, but it's up to you.

Truthfully though you really oculd pull a drive in 10 minutes, pull the bellhousing in another 10 and have the thing fixed and no worries at all.

If you do it with someone who has done it before you could probably get it done in about 2 hours as long as you dont do anything dumb like strip out the gimbal mounting bolts

Fix it.... here is one I replaced not to long ago. How much longer until this would have been a major leak?

If it makes you feel better mine was way worse then that when I R&R mine......... I have 3 rips 180 degrees around the bellow

it all has to come apart to even get the cable out to replace the boot..

So I managed to get it replaced without removing the drive and gimble. It was a nice easy fix (10-20 minutes) to get me back on the water fast, but I think I put a lot of strain on the cable and cable housing pulling it out and having to work it through and around the gimble housing while keeping it connected to the drive. So definitely need to pull everything off-season and replace the cable for peace of mind. I would recommend this way to get you back on the water, but don't consider it the best approach for a full inspection/fix of the entire bellow/cable, etc. The most annoying issue was the protective tape that wrapped the original cable near the interior side of the transom (engine side). That was a bear to remove due to lack of space!!!