100% nightmare tenant that will likely get surprise roommates and a zoo of unauthorized pets while they live there and then claim "oh I didn't know that was against the rules".

Is it contradicting to be a wholesaler and a real estate agent? 

another property to the portfolio, and a continued relationship with a live long client Lessons learned?

We worked this out with our CPA and this was his recommendation so i recommend starting with 1 account and as you grow and scale talk to your CPA and banker to see what they are seeing other investors do and what they recommend for your situation

What started off as primarily a second home with the possibility of short term leasing quickly flipped to a STR first and a second home when not rented because demand is so strong right now for STR's in this area. 

A law suit runs about $25,000 and a year and a half.

another property to the portfolio, and a continued relationship with a live long client

Great way to build a business and a rolodex of listings/sellers.

Also pro photos and a PMS with listings on Expedia, Booking.com and AirBnB. 

It took some digging, working closely with a title company, and negotiating with multiple parties to get it resolved, but in the end, it was a great learning experience—and a successful deal!