This kind of govt nosiness and overreach is why I initially decided against the financial planning industry before starting in credit. you can thank 2008 and all the fraud that went on for that.

You’re definitely on the right track by planning to open separate bank accounts for each property and the holding company.

I'm curious to see if people use AI as part of their business.  

Dominic, you mentioned not being able to scale my business using Shopify as opposed to Wordpress.

I currently have a homeowners plan with Allstate and plan on asking them if they have something like a short term rental rider plan that I can add in addition to my current plan.

All those things, and more, need to be ironed out.Question 2From a tax perspective, if you put a dollar in a business and when you sell you get a dollar back, that is a $0 profit, so from that perspective there is no tax. 

Thanks @Walter Bowser - I appreciate that advice and plan to incorporate it into this first opportunity and beyond. 

I do measure my cash on cash return for my business and for each property. 

If I take a break, that part of the business cannot function effectively.  

Check out the STR forum where you'll find some great information and will see questions and answers from those who have successfully scaled STR businesses.