I never ride my Softail, it's a waste to keep it actually.

 

Having multiple bikes doesn't mean you have money. Actually it's probably the other way around!

For a while, my policy was "always buy, never sell" and at one point we had 5 Harley's in the garage.

We're now down to 4 and IF I could get what I would consider a "premium price" for the '03 RK (Garage Queen) we'd be down to 3.
Maybe I can get a good trade-in deal going on a new Tri-Glide some day but we'd still have 4 Harleys unless I trade 2 bikes in a the same time!

My '13 CVO Ultra probably gets 99% of the miles ridden these days, as my wife hasn't rode in a couple of years and I haven't had my Springer out recently either but I am planning to take it out a couple of times this season.

 

M8 RGU and a 1996 FB with side car. I ride the Touring bike the most. The FB is a bike I have kept out of fondness for it. A bike I will never part with in this life.
Touring bike gets 20-60 K a year the FB about 2-5K now days.
As for affording it . More a madder of how you spend what you have, how you budget and save. People I know spend more on drinking and weed than I do on my bikes. Good friend of mine just spent 78K on a darn bass boat. And you though bikes were expensive.
Insurance is the main reason I will not have more than two. If it is here I will ride it so I always keep them insured. I am tempted by BMW. I have come close to bringing one home.

 

Back a few years ago we had the following bikes at once:

2008 FLHX Street Glide
2010 FLHTCU Ultra Classic
2010 FXDWG Wide Glide
2005 Buell 500
2003 Honda 100 and 230 dirt bikes

My wife used to fuss all the time that we can only ride one at a time. Maintenance, tax, tags and insurance was crazy. Finally we realized that we rode the Ultra 95 percent of the time and sold all the others. We have been a one bike family every since. However with that said the wife keeps hinting that she would like another Street Glide in the garage for our short rides. She really likes that Hard Candy paint. We will see?

 

My go to bike is usually the Ninja 1000 - I'm still more into speed and curves than laid back riding (trying to ease slowly into old age). The FatBob gets the nod for shorter runs and around town errands. The Wing when my wife rides with me, and the Wee Strom for a change of pace.

 

We have a RGS & a TG. I ride the RGS, my wife rides the trike. We ride the TG when riding double, as the Road Glide isn't really set up for two. I usually am the rider when doubling up, but I get a lot of comments when riding "bitch" on the trike, lol. After 6 years of having a trike, we seem to ride it more and more.

 

I have a chromed out 01 Softail Springer for when I feel like a "Peacock" and want a little thump. I also have a 2014 Honda Valkyrie when I want to get the heart pumping. Mileage is split about evenly @ 5K per bike per year. They could not possibly be any more different.

 

I ride each one in spurts when I have time to ride anymore. Working on the road sucks but pays the bills. The Train has been down since last summer. Kind of split time up between The Bad Boy and the Sportster lately. Each serves its purpose.
Worked hard my whole life chicken. At 63 I'm enjoying spending some of it.

 

I usually try to keep 2 bikes as having only 1 really sucks. The Road Glide is my day tripper off to far and wide places. The Road King is like being back on a Sportster again, especially when I strip off TP, fairing, shield, pillion. Makes me feel like I am riding, well, almost with shorts and high top sneakers!!! LOL

 

I use my Low Rider S back and forth to work and just for quick blasts around town and my ultra for longer rides and when the wife wants to ride.