My goal is to stack rentals with the profits from flips. 

Guests think that Airbnb is no longer cheaper than hotels and in most cases it's not anymore, but hosts still need to make a profit.   

Long story short, sold my home on 40 acres and business, made a nice profit, met an amazing man who is a contractor, got married, sold his property too and we moved to the high desert of Central Oregon near a very popular year round resort town.

Depending on repairs and updates, $40K could get you close to furnishing the home, but if you want to add profitable amenities such as a game room or hot tub, it would be more. 

He could not make a profit with that high of an insurance bill annually.

It was not uncommon that they bought some of the worst houses (weird layout, dated, much deferred maintenance) in the nicest neighborhoods and then would try to relist them as-is to make a profit before ending up having to do the actual work required to the property for it to sell again, selling at a loss, or maybe making a little bit of money in transaction fees.

How do you stay profitable during off-peak times?

I remember listening to a podcast episode of someone who would rent their LTRs to a non-profit at market value so they could use the housing for people in need.

Best to get recommendations if you can, you also might find one through a professional organization for Public Adjusters such as:https://www.napia.com/custom_m...

.#1 Find one that is profitable and growing.