The deals I underwrite have been cash flowing right up until I put debt service on them, even with taking a break even amount in a refi. 

Consider property management services and tools like AirDNA to understand local demand and occupancy projections.Good luck!

I would suggest trying someone local, may hosts have find their last resort at a local insurance company.

The E-Myth by Michael Gerber- Start and operate your business with the consumer in mind... not you... not your product or service.

These hotels are almost all ideally located right on the strip, and loaded with amenities like room service, restaurants, bars, and casinos. 

Can we hear from individuals who have experienced sustained success buying section 8 rentals while relying on entirely 3rd party service providers? 

A simple search on a service like Propstream will show you what properties have them. 

He bought the property pre COVID, so his cash flow is definitely going to be different than what mine will be.The question I'm wondering if its a good idea and if the numbers make sense.Purchase Price: $100,000Down payment: $20,000 (20%)Current cashflow: $900Property manager: $90 (10%)His expense for 12 months was only $1,430 (inspections, repairs, management, eviction services). 

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

Under the Fair Housing Amendments Act of 1988, ESA's are a subset of service animal for the purposes of residential real estate.