Then you will be well positioned to maximize the rates during your busy season.Alternatively if you list during busy season, you can get more bookings when traffic is up, but you will have to drop rates to compete with properties with ample reviews.No good answer, really as it is painful either way, but it is a preference on how you want to do it.

@Lucas Moncadayes. if you buy a random property in the midwest that is on the market, there is a near 100% chance you will lose money in the short term, and won't cash flow positive for years. 

I would offer them a lease and invite them to make an offer on the property anytime in the future when they are actually in a position to buy it.

I have a good amount of equity in both as well.

In order to not have to put any of our own money into this deal, we intend to leverage the equity of my Grandma’s home as a down payment for the loan.  2) Should we leverage a construction loan or some other form of financing? 

We haven’t received a new appraisal with the updated renovations, but we’re estimating a solid chunk of equity has been added. 

I have a lot of equity in other properties.

@Carlos Cepeda Why kind of equity would you have?

Equity-Title, LLC---Ask for SueRTR title- ask for Laura Hope

Definitely, i'm not in the position (yet!)