New Hampshire would be much easier to start with as a it is very drivable and they have winter and summer travel seasons.

Were out in Manassas, great forest walks there! 

You cant camp out in the forest.

I am in Alaska, the dark winters just aren't manageable for me anymore so I decide for mental health reasons its best to relocate.

My plan is to monitor those rental listings during the fall and winter seasons, and see which units are more consistently booked.

Personally I'd disable, winterize, or remove it due to costs of maintenance.  

Cross country skiing, snowmobiling, snow shoeing in the winter are popular.

Trust: For passing properties to you and your sister, a trust may be better for estate planning, while an LLC provides liability protection.

@Philip Beckwith typically in Michigan, you can only do a tax appeal in February.The instructions will be on the back of your winter tax bill.You will need to have great comparables to challenge the City Assessor's valuation.

Income Tax Return for Estates and Trusts.