@2004 searay didn't post a serial number so don't know what the weak points of his Bravo 3 version. They had different issues over the years.
Yes there is a problem with leaking, no it won't heal itself. I've seen many techs pull fish line out of prop shaft seals (and been guilty of doing it myself) and they always come back. Anytime lube is leaking out and water is getting in, the grease that's packed between the seals gets washed out. That grease is pretty important.
Does it need a complete reseal? Depends on the age and hours. Anything 5-6 years or older will get a complete reseal when it comes into the shop (we have to warranty the job) friends and family I'll do prop seals, bearing carrier or rear cover up to 10 years.
About the only time I see anyone get lucky is they didn't do a good job cleaning the flat surface of the hole during a lube change or they still have the O-ring style plugs and someone has been using gaskets on them --- works for awhile and then starts leaking.
Based on the lube color, this is probably just sucking in a little water during cooldown. Have you cleaned the remote drive lube bottle lately? They can plug up and not allow the drive to "breathe".