But again its about recommending to them to pack a sufficient food and drink supply if a storm is possible.We also to try have ice melt and snow shovels on hand, extra blankets and stuff like that.To mitigate some of this think about a full time back up generator to keep the power.  

Many times, dealerships will use the same movers and installers for their homes.

Providing them with ample notice allows them time to plan and adjust financially.

If you are already discounting I would not negotiate further, but I am in Tampa where I can pretty easily find other tenants / guests, so I guess it would depend on how important their tenancy is to you at this time. 

If you hand write it will take more time.

I understand at this point there will be a loss I will have to incur, but I am looking for thoughts on if I should rent (knowing I’ll have around $5k a year to loose with renting and property taxes , but giving myself time/ hope of appreciation) or if I should just sell (locking in a larger loss on the property now).

My intention is to live in the basement, rent out the remaining bedroom to a long term roommate, and run the upstairs as a full time STR.I'm aware that the City of Littleton has strict short term rental regulations, but they do allow STRs as long as I have a license and I am occupying the property.  

Thats another key factor to be able to pull out your initial capital and the next homes DP in a shorter period of time. 

I am currently surveying the NC market for a 3bd 2 ba home that is predicted to appreciate over time. 

Just let me know what time works for you.