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

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.

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?

.#1 Find one that is profitable and growing. 

If you're planning to sell it and split the profits with the seller, it sounds like you would want a novation agreement. 

Money meets effort = very nice life changing profits. 

Clark-Fulton seems to be a very profitable market.

My comments is on taking action and the profit centers of real estate:With real estate, time evens out many bumps, including paying too much.