I go the opposite of Ted and Ryan, and usually get the tailstock out of the way when I reverse the piece and put it in the chuck. On very large bowls (or dicey wood) I might leave it there for a while, but in general I get it out of my way. This is all reliant on having a good tenon and a good grip with the chuck, of course.
As to the size of the tenon, there's nothing that says you can't flip the piece around and take a bit more diameter off the tenon. A common mistake many new turners makes is being afraid to remove wood. This is especially true in regards to form (where guys will make a bowl shaped more like a cylinder because they're reluctant to remove enough wood to make a smooth curve), but it also holds true for tenons (and bottoms of bowls).
My solution to reducing the number of trips to the grinder was to start collecting bowl gouges, lol.

I've got 5 main bowl gouges, and I'll usually sharpen them all at the same time. I'll use one until it starts to get dull, then switch to a sharper one. When that one gets dull, I'll go to the next. When I run out of sharp gouges, I go back to the grinder. Even though they are different sizes ranging from 3/4" to 1/2" and two different flute shapes (V and U shapes), I use them fairly interchangeably for the most part.