@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.

Then usage is above that.

If that's the case, be sure to get some quotes for what razing them would cost as the disposal and equipment fees would be several thousand dollars.Sometimes a local fire department will burn down a building for "practice" but nowadays that may create too big of an environmental impact.If you could pick up that property with it's present usage, can you envision a "highest and best" different usage for that much acreage in that area?

@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.