Re: gas/oil mix time frame
The only stabilizer worth anything these days is StarTron. You have to treat the Ethanol in the fuel these days more than you have to worry about the fuel going "stale". Stabil makes an Ethanol formula as well, which is pretty good, but I am loyal to StarTron after years and years of use, and seeing first hand how well it works. Regular Stabil is useless for preventing phase separation within Ethanol fuels. It won't matter how long it keeps your fuel "fresh" if it doesn't treat the Ethanol in the fuel and prevent Ethanol related problems.
I'm not sure if you are talking about using a 55 gallon drum to fill your boat throughout the season or if you have a 55 gallon tank on your boat, but I assume it's a drum your using to fill you boat tank, since you say 55 gallons will last you 3 months. 55 gallons will last me a weekend, or a 1/2 a day if it's an ocean fishing trip, so I've never stored that much fuel other than in my boat, and it doesn't last 3 months.
My brother's boat has a 250 gallon tank, he fills it in the Spring and it lasts him until mid-end of the summer usually July sometime, he doesn't use his boat for many long trips, just out to the bay and anchor and back. Because of this I double treat his fuel in the Spring with StarTron because I know that 250 gallons will be sitting in the tank slowing getting burned for 3-4 months, by the time he puts more in, there is about 50 gallons left which gets mixed in with the re-fill.....in over 20 years he has never had ANY problems.
Now on the issue of the 2 stroke oil coming out of mixture, you should probably not spend any amount of time worrying about that at all, that will not happen in 3 months, or 6,7,8 or 12 months. And if for some reason that does concern you, then just go ahead and re-hook back up your oiling system, (VRO, OMS, not sure what motor you are running), I'm not even sure why you would disconnect it anyway, they are completely safe and reliable, please, please, please DO NOT listen to all the BS hype about them being spewed by "internet mechanics" who have no experience with them or have any idea of where the BS rumors came from.
I have been running these systems on all types of engines since they first came out, and have never had or seen any major issues caused by them. Some of the original systems had some drawbacks, but they were blown WAY out of proportion by bad, dishonest mechanics trying to get more money out of people. There has been countless amount of discussions on it here, if you Search you will see plenty of experts explain why they got the bad rap they did. ANYBODY who says they aren't safe or anything to that effect, has absolutely zero idea of what they are talking about. I would say that there probably CANNOT be a safer system than what is already being produced. In fact I don't trust a person mixing their fuel as much as I would trust any automatic oiling system. I've seen way more people forget to add oil or not add enough, than I have seen issues with oiling systems.