But if you can finance a home in an appreciating area make it breakeven and at some point (as always) either rents/nightly rates will increase, interest rates will go down, or both. 

- The increasing cost of damage repair and potential mold growth

I can mark it up with a fee or by increasing the rate (or both, but I never do).

This demographic is projected to keep increasing over time, so I would do whatever you can to hold onto this property (ie cash flow well).Furnishing 700 sqft with PB or West Elm (you and my wife would get along great, Bonnie) won't be price-prohibitive and well worth the cost.

There is only a $3 difference increase to move to RentRedi, but the customer service is amazing.

Ideally a HELOC is used for less then a  year project where you can refi or sell to pay back the HELOC. 5 years is a long time, things can happen and if you reduce the cashflow on both properties you'll be increasing the risk and having thinner margins.

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.

We are always looking to add more amenities and chances to increase our guest's satisfaction at all of our units.

Lastly, if you’re currently taking a homestead exemption on property taxes, once that drops off (if you’re currently taking chose to transfer the exemption to your new home) your property taxes will likely increase $1k-$2k thus increasing your monthly mortgage.

Do you think the area will increase in value?