So far I've marketed on FB, through my own network and on a rental site that shares to several others like redfin... etc.

So there isn't a tax benefit that I am aware of. 

I don't know how difficult it is to simultaneously execute because I've not personally done so.

So far I've discovered that we will need to acquire multiple permits and an STR license in order to legally list our property as an STR in the Baraboo, WI area.

I'm assuming my friend has the right to do so since the tenant hasn't paid their utilities, and they are officially no longer a tenant but a squatter until the sheriff comes.

"Hi there, Hope you’re having a great week so far!

It all will come down to the financials on these deals, and with a larger mortgage, expect less cash flow, so if I were your agent, I'd be focusing on making sure you have an income cushion but giving a broader focus on appreciation.

I’m located in DFW, so feel free to reach out if you have questions or need advice—happy to help however I can!

I have a 90 day option agreement, so doesn't this mean I can list it as the owner?

So if you had 150k, you could build and own 10 houses.