It sounds as if he's operating like a short term rental.Also if the units are being rented weekly how on Earth is a tenant several months behind?

I'm also curious if anyone had any luck with short-term rentals. 

Colorado Springs is finally getting around to drafting an ordinance for short-term rentals/Airbnb/VRBO, etc.

I live on the west coast so I'll be doing this from a distance to start with a planned market visit over the next few months. 

Long story short no

Short answer: it’s unlikely you’ll have any issues since it gets automatic consent form the IRS.

I like the trust avenue for each property.Also, if i buy it outright, and sell it before a year, i pay short term capital gains on every payment received.

Here's general info on the options-https://www.biggerpockets.com/renewsblog/2012/12/2...If you go the DIY route, there's that long-distance investing eBook that just came out on here recently (I forget the author...David someone?)

My husband and I are looking at an investment property that comes with a tenant locked into a lease until March 2019. After crunching the number we would only cash flow $100/mo and has a poor cash on cash return but ...

We might have a short time on this planet, why make it harder by taking unnecessary risks?