At best you’ll be able to buy, through “creative” finance break even cash flow situations, which at best may begin modest positive cash flow in 3 or more years. 

(I work with some challenging populations and the extra effort has paid off in these situations.) 

Or you can try James' approach to sell before the significant cap ex items but I suspect you will be selling at a price that reflects the impending coming costs.It is my belief that you have never calculated out your sustained maintenance/cap ex costs and truly believe this has positive cash flow.I am trying to provide some insight as to your view and to your situation. 

I also didn’t have direct access to him, so if I needed immediate counsel on how to handle a situation, I had to email him and wait to get a response usually a few days later, and by then the deal was already mishandled.

The Role of Mortgage Brokers in Real Estate FinancingMortgage brokers act as intermediaries between you and lenders, streamlining the loan process while finding the best deals for your unique situation.

This question never has a "best" answer, only best for your situation!

You need to have reserves in either cash or credit regardless of the situation. 20k can go away in a blink.

Personally, I would keep the property but I don't know your situation and if you could better use the money elsewhere.

last thing I would consider for this type of situation would be how are the neighbors?

Premiums in Iowa, Minnesota, Montana, Utah, and Washington jumped by more than 20 percent.The insurance situation is especially serious in California and Florida.In 2023, around 7 percent of realtors saw deals fall through due to insurance issues, with the share jumping to 13 percent last year as of October, according the California Association of Realtors.