Someone going through a divorce, someone just getting out of rehab, traveling salesman, that sort of thing. 

Our lifestyle has us consistently traveling, and while we make good money it isn't sustainable long term.

@Jordan MoorheadAs a Minnesota (temporarily a Wisconsinite) I've subscribed to the cabin religion my whole life and my near-retirement parents are trying to understand how to afford their own to retire with (religion makes us do crazy things ;)As near as I've been able to good naturedly guess, the cabin love is what you get when you mix the seemingly universal desire to travel with the home-body reserved demeanor of Midwesterners.

The research I have done so far indicates I could double my monthly cash flow doing this and have a free place to stay when I go on vacation in Maui and be able to write off any travel expenses incurred to 'check on' the condo. 

Initially his only expense was car payments, and he had a job travelling and had meals and entertainment on the expense account.

@Stefan HoltEase and affordability of travel from tristate areas.

It may sound like a waste of money but while active duty you will be a dabbler and traveling, you’ll lose substantial money by not establishing a team.

I have an opportunity to buy another underpriced investment property which should bring me 5% to 8% cash on cash return, cover expenses and then some, and the ability to write off my travel expenses on a quarterly basis.

My passion is traveling and I am going to work for the freedom to not be tied to the American standard of two weeks of vacation time (which typically must be approved by a superior, no less!).

Through years of 50+ hour weeks, lots of travel, and raising 2 kids, we actually managed to save money, most of it invested in the market.