Hey @Trysh Wahlig it was good to see you at the meet up last night.

I would be offering listings containing cash buyers within the last 6 months in designated area with all of their information, list of each house purchased and for how much. 

How can I find out whether the roof will last until then and not cause any damage to the interior?

I closed on that last week and I want to put most of that money into a down payment on another house. 

RailRoad which runs the childrens train the "Polar Express" through the end of the year and keeps town very busy with some 70k plus visitors.I would echo most of what Amy had to say about the biggest factors to consider for a mountain rental would be  accesability, view, hot tub, fire pits and lastly we have seen a shift from people wanting to be remote to being closer to town.  

In this environment, I have been hearing that we are closer to a top in prices than the bottom - across the US, due to the nice appreciation experienced during the last few years.

Surprisingly, I called a few lenders last year and most responded they weren't interested in investor financing right now.  

My wife and I are house hacking our 2nd property in the last 15 months.  

and can a Roth IRA be rolled into the Roth version of the SD-401KI too have a SDIRA and last year filed a 990-T and overall the taxes came out to just above 10% paid on the income after deducting all the expenses

The next step would be to work with the Realtor and determine the hot markets, in your County, with the greatest number of sales over the last 90 to 120 days.