It’s a gamble, but just looking for ideas from more seasoned real estate minds.

With my 2 bed I get a fair amount of advanced bookings but nothing like the 5 bedroom. 

Overall, I'd say this is a fairly normal deal.

My desire would be to tender a contract to purchase the property, pay off their loan while ensuring the owner receives fair compensation and I receive the house.

I'm thinking Sherwin Williams Alabaster (SW 7008) and white windows, and it's fairly common and well reserved in our region.

Yes, this is fairly common. 

We were fortunate to get the ball rolling fairly quickly and only have to fork out 1.5 months of mortgage on our own. my partner thinks he can do all the taxes for the home and depreciation on turbo tax, as that’s what he’s been doing forever since he’s a w2 earner.

Irs determination “You're considered to use a dwelling unit as a residence if you use it for personal purposes during the tax year for a number of days that's more than the greater of: 14 days, or. 10% of the total days you rent it to others at a fair rental price.”

I'm fairly certain the listing group is also the property manager so I'm not sure if that's a pro or a con.

I know its expensive but you will be well protected :)Or you save a lot of money and be better protected by doing this consistently and well:-carry appropriate types and amounts of insurance-sign contracts with indemnification provisions- obtain all necessary licenses and permits to operate your business-ensure all vendors/contractors are licensed and insured and list you as additional insured-sign well drafted and fair leases and be a responsive landlord -be an active owner or hire an active PM  who avoids or at worse timely eliminates premises liability exposure The strategies you often read about are sold by alarmist asset protection companies who fail to disclose how impractical they are.