I added a pool and did some landscaping and have been using it as a family winter retreat and renting it to a STR operator the rest of the year.

yeah the tenant pushing back is my concern. it just so happened that this happened with the tenant that seems to not like paying. and the heating is electric and this winter has been extremely cold which caused the electric bill to jump up to $800!

., for estate purposes), that value would serve as your basis. 

Winter is tough in a lot of areas.  

Purchase price: $1,485,000 Beautiful estate-like property in the Redwood forest above Santa Cruz CA.

I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

We have cold winters in northern NH.

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Carpet throughout (as Minnesota gets frigid in the winter) What was the outcome?

Winterizing Your Home: Tips for Draft-Proof Windows and Doors" – Offer seasonal advice."