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?

I don't know about you, but in 30 years I'd rather be sitting on a million-dollar asset that I own free and clear (because someone else paid it off for me) that is generating multiple, multiple times the rent I was collecting when I first acquired it and in which I can fill a vacancy with a qualified tenant within two weeks because the area is so desirable that it can't keep up with housing demand than on some boondocks asset that I only purchased because it was the cheapest thing around and "cash flowed" $200 per month on paper but barely appreciated over the years and whose rent appreciation has marginally kept up with inflation and takes me three months to fill a vacancy with a "qualified" tenant who even then might get behind on rent because his hours were cut at the gas station 30 miles away (true story; my tenant worked at a gas station in Boron--only job he could find).Personally, I'm keeping my 4-unit in Santa Clarita and investing in development deals and notes until an incredible off-market deal lands in my lap (keep dreaming, Logan) or the SoCal market cools.  

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. 

I do like the more expensive markets like because of the higher dollar margins and stronger appreciation.