A formal business built on this seems overkill as you’re essentially paying someone for a service that already has standard model.If you and the parnter have distinct business tasks/abilities (i.e. not what you would hire an agent or contractor for), such as off-market lead generation, that’s a different discussion.

Based on your current assumptions, you would be paying $1,229 per month out of pocket, leading to negative cash flow.If you’re house hacking and living in the property, it might still make sense because you're paying for housing anyway.

Many of the OTAs and lead gen sites, like Furnished Finder, are pushing credit card payments. 99.9% of the time I get a message from FF saying 'your tenant would prefer to pay by credit card so activate Stripe now!' 

My friend spent $81,000 on marketing and told me he could not trace one sale to a lead generated by the program and that the program generated almost no leads anyway.  

Where these numbers are found, there is a very high rate of rent actually being paid.Here is a video where I analyze a property in the Detroit area if you/anyone is curious.

Taylor often didn't communicate clearly what she needed, either to ourselves or other vendors, leading to misunderstandings and repeated clarifications and requests.

Building trust can lead to better negotiations and more opportunities in the long run.Managing seller relationships is about clear communication.

Does anyone have any leads or insight on how I might be able to acquire both properties? 

This also leads owners to ASSUME simpler is better when it comes to management contracts.

I'll watch a few videos and see what I can learn.