The reason we switched to STR and extended stay after the remodeling was because we were unwilling to deal with tenants who HATED our unit but would not move.

But self-employment has costs most people do not understand and/or, after a taste, are unwilling to pay.  

Some might be unwilling to do it since there is nothing in it for them. 

Most buyers are unwilling or unable to take on another loan while purchasing a home.

If the current owner is unwilling to get the problem tenant out, then If I liked the deal otherwise, I'd adjust the price to cover the cost of getting the problem tenant out and cleaning up after him.If you have the tenant's full name go look at court records for all the munis in the area and see if the tenant already has evictions then you'll have a better idea of what your dealing with.

If the company has a representative unable or unwilling to answer certain questions, that should be a cause for concern.

Currently this is what I envision for the structure of the deal:EQUITY SPLIT: Capital Investor gets 100% of his down payment, and then we split equity 50/50 from there.CASH FLOW SPLIT: Totally unsure as to what is/isn't fair but seeing as the market rate for airbnb management is already 20-30+% and I am bringing the deal to the table I feel as though 50/50 cash split wouldn't be an insane request.SELLING: Upon one of us wanting to sell out the other would have an option to buy out the other partner's equity, and if unable or unwilling to do so we must sell the property.

Currently this is what I envision for the structure of the deal:EQUITY SPLIT: Capital Investor gets 100% of his down payment, and then we split equity 50/50 from there.CASH FLOW SPLIT: Totally unsure as to what is/isn't fair but seeing as the market rate for airbnb management is already 20-30+% and I am bringing the deal to the table I feel as though 50/50 cash split wouldn't be an insane request.SELLING: Upon one of us wanting to sell out the other would have an option to buy out the other partner's equity, and if unable or unwilling to do so we must sell the property.

The top objection is  that HoA won’t allow short term rentals.We have talked to them and they are unwilling to do anything less than 1 year lease.The seller isn’t willing to go down in price. 

For me, I'm unwilling to do this as it directly goes against on of our core values of being the easiest private lenders to work with.