For a rental property, the gain is subject to capital gains tax (15-20%) and depreciation recapture tax (up to 25%) on any depreciation claimed, unless the proceeds are reinvested.To minimize taxes, consider reinvesting the sale and insurance proceeds into another property under §1033 or converting the property to a rental before selling to claim depreciation deductions.This post does not create a CPA-Client relationship.

There is only a $3 difference increase to move to RentRedi, but the customer service is amazing.

My only complaints with their customer service are 1.

If not, I most definitely would reach out to the tenant, introduce myself and ask if they are going to be out by the 31st or the 1st, I would communicate  to the tenant as if I know they were told they are expected to leave, otherwise you may find they "do not know" they need to leave even if they actually know they need to leave....In the case they claim they are not aware they need to leave, you would need to follow the laws in the state you purchased the property, usually you can find that info on the states judicial branch or speak with a landlord tenant attorney. 

The programs that claim high success, over and over again, are the ones that appear on these forums a few years later with students making claims about misrepresentation by the programs. 

A reasonableness standard is applied to negligence claims and I would argue a property owner who owns real estate in the Poconos and knows the property is left vacant due to the owners decision to lease the property as a short term rental should know that the pipes are more inclined to freeze and therefore should install heat tracing lines or other measure to ensure the plumbing lines do not freeze.

I updated the kitchen with high-end appliances, installed custom cabinetry, and added modern finishes throughout.

They claim they do all of the marketing, connect with the leads, negotiate the deal, and close it.

Based on your experience, would you agree with that claim?

Before making any decision, I would get a customized property evaluation by a local Realtor to determine the value of the property on both sides of the spectrum; sale OR rental.