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.

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.

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?

Aside from the fact that I'm going to get fined on not paying it in time (and since their deadlines are so short, I don't see how I can ever get out of that cycle yet), any ideas how to pay it?

The idea would be to buy a house for short rental (AirBnb or longer period). 

For a 3 br 2 bath, depending on the area, I’ve typically seen 800-850 for rent.I think that combined with the financing being on a 20 year amortization is where this deal falls a little short.