We acclimated the flooring, but I suspect the existing tenant may keep the house at some very different temps (when she travels I suspect it's quite cool in the winter just warm enough to keep pipes form freezing, and very hot in the summer).  

You're missing the forest for the trees.Sure, it'll cost you to go after them.

I use the home about 2 months in the winter and a few 10-14 day stays during the year.

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Usually during the late fall and winter, particularly from November to February.

I hope all is well.We have a STR in the town next to Ludlow and we were booked solid for the Winter (every single weekend and many weekday nights.)Check out our property "Honeypot Farmhouse" here.We're just coming out of "Mud Season" now where everything shuts down (restaurants, etc), but entering the Spring and Summer, we expect the rentals to pick up nicely.

Sea Pines and Palmetto Dunes continue to bring the highest price points, but the Forest beach area is also a strong area.

She's willing to pay a premium for the month-to-month arrangement.I've never done a month-to-month lease before and I'm worried it might be a hassle, especially since I don't know how the market will be in the winter.

You will also find that the dates of October to March are very slow in the winter and often times people turn them into medium term winter rentals in order to keep them occupied.