The additional security deposit (double the normal), I would do during the winter months when demand shrinks. 

How is the cash flow in the non-winter months?

I did most of the work myself, weekends and holidays.

Sellers don't want to deal with the secondary FHA inspection, and then have to do for example exterior paint in the middle of the winter, having to delay the closing. 

Just a thought Nicole about South Dakota is that exterior work slows way down in winter. 

One thing we will do on winter flips is add a landscaping clause in there so that in April or May, we'll come back and reseed the yard and give them a $200 allowance to purchase plants and we'll plant them if they want to. 

Also, on a complete side note, is it a red flag if a property in the north-east doesn't have a heating system for a period of time in the winter? 

I am looking in Sarasota specifically so that a family member might always have a place to stay during winter months.

When a furnace dies in winter or a tenant decides to take advantage of an eviction moratorium you better have access to cash somewhere!

However, the surge in coronavirus cases in the early winter made the slowdown more pronounced.