Someone will need to be handling inquiries, monitoring rates, guest issues that arise, marketing, repairs, maintenance, and housekeeping. 

The brokers will have the best pulse on the market - I'm an investor & broker in NYC and can attest that because I'm in the trenches, I have a good sense of what the ARV is on a property. 

I also think that we are very close to a 1929 Market crash, and everybody seems to think that we are doing great.

I'm also open to other markets as well.

If I'm in your shoes (which I was a few years ago) I would recommend attending at least 1-2 real estate meetups a month to start putting yourself out there and networking with other players in your market. 

Additional Information:Any advice on navigating a market move with ongoing investments would be greatly appreciated!

We do place this information in our marketing so we're transparent on expectations but that way if 2 of the 3 can financially qualify on their own and have good credit, the third may be a bit of a risk but at least the other 2 are in good standing.

If you are adamant this is how you will scale your business, I would overemphasize the importance of systems because the BS minutia operating real estate in these markets will be greater than in higher barrier markets where greater operational efficiencies exist. 

Currently, we have learned a lot on how deals happen and what it takes to be a competitor in our market.

Take a bold approach to the real estate market.