Advice: unless you're comfortable with doing it (like you've done it before) I would suggest you pull the boat to do it. Failure to get it done correctly and in a timely manner would mean immediately pulling the boat. That's not to say it can't be done in water, you just need to be aware of the risks. I have done it once but I don't advise folks doing it.
For the time being, you could tighten the gland nut when not using the boat to stop all water flow and readjust it only when using the boat. Of course, some are far more accessible than others. Mine is particularly easy to do, others are nightmares.
You may also want to consider a PSS seal for your shaft. They work flawlessly and need a minimum of servicing. This will require pulling the boat for sure.