Here are some situations where it might make sense, along with considerations for how long one might wait for the situation to improve and what margins might be acceptable for a flip:Expectation of Significant AppreciationStrategic Value or Unique OpportunitiesMarket Rents Expected to IncreaseFix-and-Flip with No Rental StrategyConsiderations Before Buying with Negative Cash Flow:Financial Resilience: Make sure you have enough cash on hand to meet the shortfall without endangering your overall financial situation.exit Strategies: Establish practical, well-defined exit strategies.

They are all on the same sports team and have no "proof of income."

Your property sounds to be more unique, therefor likely making it challenging to find acceptable comps. if the property is common for the area, it's likely this could be a non-issue with the right lender. 

And when we had our last housing crash it was a very unique time.

I gathered all my notes in a 50+ pages document touching on formation and maintenance of LLC and business structures, transferring assets, protection strategies, trusts, anonymity, insurance, levels of protection, etc. including when you should do it, how many properties per LLC, due on sale clause, selecting an attorney, fees, checklists and resource materials.There is no absolute answer and unique tool/strategy in anything real estate.

Leveraging an FHA 203K loan for house hacking is a smart move, especially with your unique position in a market with unmet demand for student housing page link.

. --- You're right it is a unique perspective....

Each situation is unique so I agree - alway ask for professional advice!

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There is no timeframe for repairs because every repair is unique and will have it's own set of challenges.