In Milwaukee it is the harsh winters.

Cashflow is tight right now because the winter season in my area of Maine is a lot slower.

It's snowing here in metro Detroit today, and more is expected over the next few days, so stay there in South America a little while longer if you want to completely avoid this winter.

I currently own and operate two STRs in Minnesota (1 in the Brainerd Lakes Area and one in Duluth) and think owning a vacation rental in a market where the winter and spring are the busy seasons would be nice to offset my current slow seasons being in northern Minnesota. 

Thanks to all who've responded - these are all good thoughts and great advice.The only timeline for completion is that the house is just sitting there and I'm paying taxes on it and will be paying to keep it heated this winter. 

I might try to time it with one of my breaks (3 weeks each in summer and winter) so I can focus on the rehab.How? 

A lot of people in this market swear that it's still going to get higher, while a few financial "experts" seem to think that "winter is coming" (a correction).Besides the regular investment strategies (which I'm starting to implement soon), I really have the bug to put that FHA to work and get started (this would be my 2nd property, first is already a rental in Austin), I just think I'm missing something and I'd like your opinions. 

If you are going into the winter months it's good to have it tenanted.

I was concerned about the potential electric bill because winters in Wisconsin can be pretty brutal.In reality I kept the temperature at a comfortable level and never had an electric bill that went higher than $90 to low $100s.i loved it.

If the estate was not probated ,your sister could petition the probate court to be executor for estate.