You may pay $10,000 in interest but you only get back $2,000 back in tax savings. $2,000 is just a random number, the exact number depends on your overall tax situation.Building an ADU if you plan to rent it is business interest, not personal interest.

Blaming Loopnet for an allegedly bad property manager is like blaming Zillow for an allegedly bad realtor...I'm sure if Loopnet was stupid enough to give ransom money to BBB, BBB would take down the bad reviews and un-filter any good reviews (which is the entire business model of BBB).

If you have the money find the top player for sub to in your area and partner up with them, just make sure you got a great attorney to help structure the partnership.

May be in Texas it's a good way to make money.

I lend money privately and would never consider this as it is dependent on things out of my control (permits, neighbors, you being a good host, rental demand etc) I sell a ton of STR that are in actual resort communities and have great amenities and they are all  competing for the same guests, I can't imagine that there is a need/demand for this type of unit.

I hate to say it, but this is when a PM would be really valuable and you need to decide if the stress and time suck is worth the "savings."

If you are raising money you will need to register the exemption with the SEC, and it will depend on whether you are using accredited or non accredited investors. 

Gentrification of the West Loop & West Town is complete so the money is moving west- i.e.

If I pay with cash it will take up most of my money that I have set aside to perform renovations on the property.

It may not make sense for your personal finances if over invest and end up with a house hack option that costs more money than somewhere you could live on your own.2.