These properties don't really have negative cash flow, except when evaluating based on the asking price.

I've looked through recent sales (trailing 12 months) to determine similar cottages with similar lakefront amenities, and although none are as small (most are 1000-1500 sq ft), I determined what I feel is fair market value based on cost/sq ft.

@Stevie Nosekabel is your company based in Ohio or based here in Texas?   

The real question is how much interest rate and how many points based on your specific profile, which will become clear when you provide all your information to a mortgage lender? 

@Zachery Hitchcox & @James Thomas:Although there's a small group of us here on BP who are based in Japan, I do not recall seeing this topic before. 

Making $25k over summer concerns me based on the estimated value of your home.

This is a complex topic that varies from person to person, so talk to your CPA.

These loan don't let you close in your company name because they are based on you.Portfolio - I'll define these loans as loans that come from the bank's own "portfolio" of money.

You may want to see if you can claim real estate professional status now or sometime in the future based on your participation within real estate of being a landlord in addition to being an agent.You may want to have your past couple of returns looked at for review to see if they were done correctly.

Find someone fee based who can talk you through what your finances and options could look like if you do or don't sell all or some of your properties.