I'm Curious what it is that he should invest into specifically?

Is there a specific property or strategy you’re going for?

Every market is different, and I won't speak to Cleveland specifically, but for my clients in Chicago, a house hacking strategy is often more about appreciation.

Just a quick question for the forum's sake... do lenders take into account specific job titles/responsibilities when decision making?

Perhaps you can find one willing to take on the project, someone who really understands your specific concerns.

Many Commercial lenders are not licensed, since there is not a specific license to originate 5+ Unit Commercial loans. 

I'd consider utilizing the tax experts option on turbo tax if you have any specific filing questions.

So I’m buying, adding capital improvements that are specific to aviation operations, then selling the hangars to the avionics company.  

.- every investor reaches a point where their DTI is trashed and they have to move into different loan products. there are tons of lenders out there that specifically work with REIs & have many ways to navigate this. don't let DTI concerns keep you from moving forward. - LLCs provide minimal legal protection in case of an incident. work with an asset protection attorney to come up with a better plan if they are that concerned. also have great insurance and an umbrella policy. 

-Any other specific tips for the Tampa market would be welcomed!