I'm ultimately having an architect get back to me regarding what the city plan checker states in my city. 

You were trying to help but you likely put them in a bad spot that will ultimately hurt them.

I know it's a risk using any private lender, but what are some initial questions I can ask to get a better idea to make a choice to use one if any? 

This gave me the option to be a stay at home mom when the day comes, and makes the choice for him to stay in the marines when his time is up a real choice.

While that may be the direction you ultimately decide to go, something like the BRRRR strategy could help you take that money and turn it into multiple cash flowing properties. 

As I'm not sure whether they will close, I usually build in a safety net of one of the choices being a Delaware Statutory Trust just in case the targets fall through. 

Ultimately, I'm trying to squeeze more rental income out of my SFR which is barely cash flowing right now.Edited to add: is there any way to look up online how many properties in a particular area have ADUs?

There's always more than two choices.

Cincinnati, OhioDayton, OhioToledo, OhioYoungstown, OhioCincinnati, OhioMemphis, TennesseeSaint Louis, MissouriIndianapolis, IndianaDetroit, MichiganErie, PennsylvaniaLouisville, KentuckyMilwaukee, WisconsinJackson, MississippiI am guessing you've already seen it but in case you haven't check out The Ultimate Guide to Grading Cleveland Neighborhoods to help you as you continue investing in the Cleveland market. 

Biggest need is on valuation methods/tactics, but we ultimately want to develop a playbook for new partners to plug into!