I have a 2007 Stratos 285 w/ surge brakes (disc brakes). I had oil leaking from my bearings after my last tournament last year. Put it in storage for the winter and when I took it out of storage on Monday of this week I took it straight to a marine service shop to have the bearings / seals inspected. They replaced the seals and hubs and I picked it up later that day. I drove it home no problems but after it sat in my driveway for about 45 minutes I noticed oil again leaking (a fairly heavy stream). I left it over tonight because the dealership was closed and the next morning I left the house with the intention of taking it back to the dealership. I got about 5 minutes from my house and noticed smoke so I immediatly pulled over.....considerably more oil was now leaking and a little bit of oil from the other side. I parked and disconnected it a businesses owners lot with his permission. The dealership sent out a guy to inspect it and he again replaced both hubs / seals and said he drove it around for about 15 minutes with no leaks. I picked it up on my way home from work and when I got it to my house (a 5 minute drive) and inspected things there was no oil leaking but my rims were HOT AS HELL. If you spit on them the spit would boil. I jacked up the trailer and the wheels spun fine so I don't think the brakes were sticking. I let it sit for about 3 hours and then took it out for another short spin and it did the same thing again.....no oil leaking and no smoke but the rims on both sides got hot as hell. I wasn't riding the brakes, the trailer doesn't lean forward/downward when I trailer. Any suggestions?
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Sounds like it would be brakes draging. But you said you jacked it up and both wheels turned fine. Hopefully he filled them with oil. But it still sounds like brake drag had one side do that to me stuck piston but not both. You may want to try bleeding the brakes. Just my $0.02. 
