What programs/tools/resources have you found helpful for things like:Finding areas that are most likely to increaseFinding the best size or room numbers to optimize profitAny other areas that would be good to knowThanks in advance

In that situation, the dwelling unit is never disposed, and that is the essence of the dynamic you're trying to examine.Now, with the situation at hand, you're talking about a lot more than just scrapping the mobile home, so the optimal answer given the facts and circumstances would depend on a conversation with a tax advisor who excels in this area. 

It’s not a bad decision giving everyone you have stated but it’s certainly not optimal either.

Selling the existing SFR sounds like a pretty sub-optimal idea now :) @Austin Largusa investing out of state is absolutely on the table!

To be honest, 30+ minutes on a dirty CTA each way is not something I’m willing to do, I work 70-80h a week (that’s my “little sacrifice” already) so it is important to keep my daily routine optimized, and walking to work from River North/West Loop is not negotiable.That might as well mean that it’s better for me to keep renting rather than “investing” in an overpriced condo. 

.$3,000/month x 12 months = $36,000 annual ADU rental income$36,000 income – $5,400 expenses = $30,600 net annual revenue$30,600 revenue / $225,000 investment = 13.6% annual returnHere are some things to consider with regard to ADU amenities to optimize rents:Storage: ADUs are generally pretty small and usually don’t include a garage, so it’s important to include areas for tenants to store their belongings.

Since my work allows me to go remote, and work form anywhere I can use that to optimize living in that area.

I prefer to self manage STRs to optimize pricing and guest experience.

(5) and finally, do you all have recommendations for loan agents / officers who can help us think through what would be the optimal path for us given our situation?

As for the loan side of things yea I agree though if I can get it done with an FHA 203K I would say that would be optimal though perhaps not practical.