It's not investment, and it's certainly riskier, but it's not some absurd concept.Leasing an item to use in business is pretty standard.I don't see why leasing an apartment or house to use as a short term rental is any crazier than renting a crane and using it in construction.

My Father has been renting us a house in OBX every summer since I was a kid and were both pretty affluent now and I'm floating the idea of us going in together on an Oceanfront somewhere in OBX that we can use a few weeks a year and have it pay for itself via rentals the rest of the year. 

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

You find out up front if they have any cash or not, vs burning 30-45 days to find it appraises at your listing price, and they don't have the cash to close.Get a VA checklist from one of your trusted lenders and make sure everything in the house meets the checklist. 

I did that with my parents and it worked out perfectly when i bought their house.

I'd like to start small with 1-2 STR tiny house(s) or other less expensive "alternate housing" options (yurt, airstream, etc).

I allowed the original owner to stay in the house until payment was completed and was credited the $300 every month.

I have lived in the property for more than 3 years and we have been the only occupants in the home since it was built.The potential cashflow isn't the best but our primary goals were to build up the equity in the home to be able to potentially purchase other properties in the future with the chance that we may return to the house in the future.The property is in the Castle Hills area in the northern side of DFW which for those who don't know is generally a neighborhood with higher income tenants. 1. 

That's what open houses are for.

Yes, you read that correctly, the appeal can go either way or stay the same, you lose if the taxes go up.My brother appealed taxes on a house in Philadelphia and got a 12% reduction using the guy below:Jerald GoldfineRE Tax Associates of Pennsylvania LLCGood luck.