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.

While borrowing for a down payment is risky, increasing your savings will lower your interest rate.

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?

IF that is the case full stop - yes you are paying for something called insurance but if you have a claim the company has the right to pretty much deny coverage for having the wrong type of policy.Landlord policies are higher cost but for a reason - there is a different and increased level of risk when the house is not owner occupied.Talk with your agent and get all the details sorted out. 

That being said, there's no way your tenant will be happy with the increase so you may take that into consideration.

With $100K in cash, you could leverage this option to make a larger down payment and keep monthly costs manageable.Maximize Rental Income:Are there ways to increase rents on your current properties?

Guests appreciate functionality more than anything, so as long as they’re clean and do the job, you’re good to go.Little details like this can make a big impact on guest satisfaction.

Hoping (SD) rental amounts have increased and renting it out/refinance if able/eating the cost. 4.

I am hopeful they will want to work with me to get things repaired and updated to validate appropriate rent increases.