I am based in IL just outside of Chicago.

Loopnet has some comp information, but requires a paid (and not cheap) account to see it.Commercial properties are generally valued based on income, not comps per se. 

I'm a CRE attorney based in Nassau County although I frequently work in the boroughs as well.

Quote from @Cosmo DePinto: When applying for a DSCR loan, can you base the rent off a section 8 tenant?

If you're doing a rate and term refinance, there's typically not a seasoning period but again it's common for lenders to require it be rented first.If you're doing a DSCR cash out refi, it may not need to be rented first but you're probably paying a higher rate.Your best option is to call a loan broker you trust and go through the options based on your current situation.

Southwestern Michigan offers plenty of charm and is a destination place but would definitely make sure your ROI makes sense based on your long- and short-term goals with the property.

This is not a one size fits all answer, but bad debt is non-asset based or depreciating assets - , credit cards, medical, buying dumb stuff.Good debt is debt used to make or grow your portfolio. 

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth. 

It’s still rough and has plenty of room for improvement, but I can upload photos of a distressed property, tax records, comps, lender rates, and local rehab costs.From there, it analyzes the photos to identify repairs, explains why they’re needed, estimates costs for each item, calculates the total rehab budget, determines ARV based on comps, and provides an expected return—basically automating a lot of what spreadsheets already do.It’s not meant to replace an analyst, and of course, everything still needs to be verified.

Based on your description, it sounds like you would violate the self-dealing rule and could put your SDIRA at risk.