The Oliver is used for my worksite lodgings. I work out of town during the week and am home on the weekends. So basically 4 nights away, and 3 nights home each week. I don't haul it each week, but leave it at the job. Cheaper and less hassle than hotel rooms. Previously, I had a 5th wheel for that purpose, but it was just too much to deal with, and nearly impossible to keep warm in the harsh winters in PA. I'm glad to be selling it.
The van I use for my vacationing. Mostly weekend adventures, but I've had some longer trips. Nothing beats the B van for convenience and being able to go to odd places. I've run the gambit to visiting cities, football tailgating and backwoods boondocking. About 1/2 stealthing, the other half in campgrounds.
The teardrop I use solely for car rallies. I got to 4 or 5 rallies a year. My little sportscar pulls it without issue and it's again less hassle and less work that using a hotel. Often I can't commit to the rally with advance notice and reserve a room months in advance. With the teardrop, I can decide to go on the rally at very short notice and not worry about a place to stay.