And now we also have better marketing in place on socials and a have a direct booking site, plus we are open all year long so word of mouth is improving.  

However, the rents are slightly lower and could potentially wipe out your monthly cashflows with one major repair.As for higher appreciation market like West/East Coast, it's more expensive, but rents are higher due to a strong labor market, there will be a certain amount of demand for those markets, but the downside is that you will need to be creative by adding more values for the property.

That said, expect to deal with a fair amount of fluff leads.The two best strategies I’ve found are inbound methods: direct mail and Google Ads.Direct mail can be expensive, but it can also yield highly discounted properties.Google Ads, on the other hand, doesn’t require data extraction like calls, direct mail, or texting.

I would draw a circle around 30 minutes of you in all directions (not into the water of course) and then 60 minutes and run some data there first before packing your money up to ship off to a market you don't know.

I, along with a dozen others, teach subject to and creative finance.

An analogy would be creating a self directed 401K plan.

And I always check the actual price the guest pays- because I haven't yet build direct booking (it's on my list) and the final cost (on VRBO and Airbnb) usually makes me re-think things with a larger perspective.

Hi Eric,To be direct, this is not a property that a local, experienced investor will buy. 

Since I don’t have many assets or a lot of cash on hand, I’ll need to be creative and strategic.

I don't know if you're trying to do this all with the same lender, but if you're taking up a majority of the office buildings, SBA could be an option which would allow you potentially less down and you can get away with some seller carry (not all lenders allow and/or structure this but some do)...and/or you could potentially wrap in more collateral (like that other property) which some will do (Again not all SBA lenders are the same; some get way more creative than others).