Undoubtedly, the biggest regret is getting involved in the short-term rental market.

There is less risk involved in the cheaper properties .

There is certainly room and reason to apply different approaches and many different approaches can work well. 5.

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Be clear about your requirements before inviting them to apply.

It involves much more than collecting rent or throwing up a Craigslist ad every blue moon.

You’ll be judged and screened exactly the same as everyone else that applies.

Any excess proceeds not applied to the investment portion may be taxable as "boot."

Ultimately, it’s about the level of involvement and risk tolerance you’re comfortable with.

I hope it works out for all involved.