The target market seems to be millennials who are transient, place high value on experiences in lieu of possessions and seem to enjoy the services these co-living start ups offer.

Also, we are starting a service that manages vacation/short-term rentals here in the area. 

Good service, but they're not really in-charge of the loan, and can just escalate to FACO for you.   

When I first purchase a property, if the existing water heater is at least 10 years old, I replace it because I don't know how much maintenance has been done to it by the previous owner plus I can then start over with a new one on my own maintenance schedule.

Have you been putting money aside for a reserve to cover Vacancy, CapEx, and Maintenance?  

I also have the advantage of having some family members that can help me with the management and maintenance.

You won't get the same initial return, but you will spend less on maintenance and will have more long term growth in property value.

You want to get the best deal, but to do the most service and create that win-win of course so when a seller is telling you they need to get out, you find out why and how you can help.

I would increase your CapEx and Maintenance expenses (I use 10% each for older, lower valued properties), but I err on the conservative side. 

Yes, $1000/month is after all expenses and debt servicing.