I've walked through a property with a wholesaler and when I walked in I told him the ceiling height here is a big factor for resale and I can't use the comps he sent me.

@Abdul HafeezRates and LTV depend on many factors. 

This is a beautiful house - rehabbed/looking new and fresh - walking distance to the water etc, yet low gross yield  compared to Byrd (???)

You'll still make a premium over long term rental rates and not have to deal with a cleaner very often.With airbnbs, the beauty is not having to hire a Property Manager, your cleaners act as eyes on the property. 

While that kind of income is not a deterring factor, when I looked over the terms of service many big red flags came up.

Not sure your situation financially but even your $100,000 HELOC is going to probably run you $12,000 additional each year in expense that you've got to factor in.

Are there specific factors you look for in an area to make sure it’s a good fit for this type of rental setup?

I own a small multifamily commercial in Albuquerque and can confirm the diversity of the economic and cultural factors that you mentioned. 

We measure against 15 different factors.

In your situation there is actually another factor that may work in your favor.Only the proceeds allocated to the sale of the building can be used in a 1031exchange.