Individuals? 

My husband and I are looking to connect with like minded individuals.

I have three listings, 1. unit with a pool and hot tub, 2. unit with a hot tub, 3. both units together as a 12 sleeper.Gross monthly income (after booking channel fees) for the first unit over a 7 month period was $7309.Gross monthly income for both units over a 14 month period is $11,297 (after booking channel fees) As a long term rental the combined rent would be in the region of $5500.Is it possible to sell the property based on the income generated by the STR business or would the value always be based on bricks and mortar comps? 

If you are not attached to the duplex, could be a good time to sell to developers who want to convert to individual condo units.

Managing mix of STR and LTRs and may be starting complimentary business like cleaning and landscaping to generate more revenue.

If they were separately metered, each tenant would pay the $116.50 base fees and their individual use, which would be 3x higher than what they pay when sharing a meter.There are many options, but don't make it more complicated than it needs to be.

that will not cash flow - you won't be generating "cash flow" from the property that will go beyond servicing the debt and allow you to pay down any principal. 

He is arrogant and generates ill will.

I definitely want to have that long-term mindset and buy a property/house hack that focuses on appreciation, but can also generate some positive cash-flow after I move out.

The experience was really bad as I was getting 1-2 year old leads to cold call that I knew had a 0% success rate and I do much better generating leads organically on my own.