(Posting in the
Cars & Bikes subforum will net you more replies, probably.)
I wouldn't freak out, not quite yet.
The unit construction and shared sump means your motor oil is also your tranny oil, and nothing wears out oil more than transmission gears. There are some metric v-twins that have a separate oil tank for the transmission, which allows you to use longer lasting 80- or 90-weight gear oil. Don't think yours is one of them, though.
Another thing to remember is that your oil is not only being shared by the motor and the transmission, but
also by the clutch.
As far as your tranny jumping out of gear on its own, first check for proper clutch adjustment. There is an adjuster on the cable itself. And if you have the type that is pushrod activated, there will be an access cover on the primary/final drive cover.
You do have the owners manual, right? And after buying the bike, the first thing you did was order a factory service manual, right?
Incidentally, you should be using quality synthetic oil, if you're not already.
Lastly, join and login to vulcanforums.com. You'll get immediate answers from people who can answer in specifics rather than generalities.
Ride safe!