Every two years (more or less) I get the itch to trade my bike and get something else. My wife used to say, "Why don't you just get what you really want, and keep it?" Until I told her that what I really want is to have four or five bikes of different types. She don't make that comment no more.
But it started me thinking, if I did have the space and the interest to have, say, five bikes, with a very frugal mindset, what would I get? In no particular order, this is what I came up with:
First, a touring bike. The first two touring bikes that come to mind are obviously the Harley Electra-Glide Ultra and the Honda Goldwing 1800. There are a lot of other comparable bikes around and some of them can be had at very reasonable prices; they are "interesting" but not desirable. The Harley is a great bike, has a great sound, and buying one gets you membership in the most extensive and beneficial motorcycle club in the world - even if you don't formally join the Harley Owners' Group. A Goldwing 1800 is a superior bike in almost every way, but it cannot be fitted with floorboards or highway pegs (seriously), and it sounds like a sewing machine. I could go either way on this, but I think I would lean toward the Goldwing because it is nimbler (low CG), it has reverse, and I like the look of it better.
Second, a Bad-Ass cruiser. The reflexive answer here is a Sportster 1200, but you really can't go wrong with any number of Japanese cruisers from Honda, Kawasaki, Star (Yamaha), and Suzuki. All of these can be found with extensive aftermarket equipment, generally intended to make them look and sound like Harley's. I think I would go for a V-Rod. These have horrible resale value, and I've seen low-mileage examples around for $5k.
Third, an "Adventure Bike." The capacity to go off-road is enticing and would probably never be used, but as with car buyers getting SUV's it is a Thing to do. Again, some Japanese models are ridiculously inexpensive, and in this group, the V-Strom 650 stands out. Often the original owner equips them with bags and other cool off-road accessories, making them suitable for riding the Alaska Highway, should you choose to do so. Kawasaki and Yamaha offer similar bikes at slightly higher prices, and BMW and KTM offer superior Adventure Bikes...for three times as much.
Fourth, a "street bike." Since I'm too old for a crotch rocket,, and can't imagine myself ever being comfortable on one. For an everyday street bike I think I'd lean toward a Honda CB900/1000 or maybe a Triumph America. Both are dirt-cheap on the used market, and can be had easily for Four Thousand dollars
Finally, a "runabout" to take to the grocery store. The Suzuki Burgman is at the top of my list here. I think that the 400 would be adequate, but the price premium for a 650 "Executive" is so small, and there are tons of them around, that I think that's what I would go for. Again, $4,000 would get a pretty nice one. Plan B here would be an old Honda Pacific Coast (800). It is the most car-like MC ever made, it is comfortable, maneuverable, efficient, and packs a shit-load of storage capacity under the seat. Best of all, a very nice, low mileage PC800 can be had easily for $3 grand.
So, spending $7,000 for a Goldwing, $6,000 for a V-Rod, $3,500 for a V-Strom 650, $3,500 for an old CB Honda, and $3,500 for a Burgman: Five nice bikes for a total of $23,500.