If we sell it inside a year (short-term), his regular tax rate is still low because he has no regular income. 

Hadn’t bought my first property yet at that point.I ended up breaking contract because of the roof but the short answer is that if you are going to rent a room in a basement it needs to have egress.

The short answer is yes.

Hello, I have a townhome close to theme parks in Kissimmee, FL that is rented and on a one-year lease (was previously short-term rental).

Same thing happened with short term rentals and everything else.

As others are noting, it's important to run your numbers and would probably only recommending pulling from the HELOC for short term opportunities.

My business partners and I are looking to branch out the investing business to include short term rental management via co hosting.

Many people also rent out mid term or short term to increase their cash flow and rent by the room or unit if you buy a multi unit property.

Streamline focuses on large VCMs, such as 50+ units, not the boutique short-term rental manager/investor. 

Once you have a short list, get an account with each one and run them through the wringer to see how they really function.