Maybe we can connect sometime and talk real estate over coffee.  

Check on Zillow to see what other long-term rentals are going for in the same area - if the monthly rent you could get would be worth it for you to achieve your longer-term investment goals, then it might be an option worth considering. 

You should also involve Vrbo if something comes up that is beyond your control.I personally have never had to cancel a booking, so I don't see this as a big deal.This must be an issue for them to come up with these rules.Preparation H has a warning that says no to take orally, probably because someone did do this, so they had to create the warning.  

I own the property free and clear, and reading some above posts, sounds like that might not be an option with financing.

Otherwise it will have to be an investment property loan with about a 20-25% downpayment.The trade off with less capital is you have to be more uncomfortable with your living situation while a higher down payment loan product gets you a more comfortable living situation.

There will be an 'adjustment' at the state level if the state does not recognize bonus depreciation / section 179 expense.Best of luck.

I have a text conversation where I state "that should not be an issue" but beyond that nothing documented stating I wouldn't be holding on to their security deposit.

Having said that, I have interacted with Chris Seveney on many occasions and have found him to be an upstanding guy who is very generous with this time, knowledge, and expertise.  

If I was younger and really looking to expand this would be an avenue to investigate.

Hey TJ - we live in the same town, ElmhurstWe should grab a coffee and chat about our RE investingGerry