What a joke. 

I look at a building and if it's ugly, I go "yup, that's distressed" That's a joke, for all of you haters :-)Anyway, there's a difference between distressed and old but functional.

Property management in Chicago is no joke...I highly advise against getting into it, lol, unless you have some crazy competitive advantage, which maybe sounds like you do.We've got a small brokerage team, most of whom do not transact heavily and do some investing on the side. 

On finding help, I’d  keep an eye out for the CPAs active in Biggerpockets with proven real estate experience, or search for phrases like “short-term rental CPA,” “Airbnb tax CPA,” or “real estate investor CPA”and then filter by folks who talk specifically about STR material participation and cost seg in their content. 

By the way, this's a joke.

An earlier engineering report I saw even used the scary phrase "structurally significant settlement."

You might want to rework your listing headline and description to highlight phrases like “future development corridor,” “R10 zoning — RV park/campground potential,” or “income-producing transitional property.”

Publishing criteria (like “3x rent income” or “650+ credit”) is fine, but it can open you up to unnecessary back-and-forth or legal gray areas if phrased wrong.Best practice:Keep your criteria written down internally (income, credit, rental history, etc.).Apply those same standards to every applicant and keep a record of your process.When someone inquires, you can share your criteria in writing or over email so everyone gets the same info — that’s what shows consistency.If you want, I can share a quick example of a fair housing–friendly screening checklist I use with my clients, just message me and I’ll send it over.

>A penny saved is a penny earnedThat is the phrase but in reality a penny saved is worth more than a penny earned.  

I finally quit the LLC business(it's a joke) and had an attorney redo my titles,  and I now simply have high Umbrella insurance coverage.