I was going to buy a owner occupied duplex with 3.5% down then buy an investment property using 25% down but my DTI ratio would not qualify for both mortgages in the same year unless I used a dscr loan but then the interest rate would be very high, and it'd be hard to make a deal work using a dscr loan because of that.

I don't know enough about your rentals to determine quality, location, or layout, but I suspect my numbers are pretty close.However, your utilities are pretty expensive in the winter.

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

Buyers and sellers should consider some amount of closing money be held in escrow after closing to cover potential problems with the non-responding tenants.Does anybody have any experiences to share with successful use of a Tenant Estoppel Letter, or times they wish they'd know about this tool before entering a Purchase and Sale Agreement?

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

If you have a high level of faith in the company you are working with, then time will do what it is supposed to do and increase your IRR.  

@Alec DresslerYou’re on the right track using tools like AirDNA, but for better data, consider the paid version or platforms like Mashvisor for detailed rental analytics.

I use the fix and flip tab and it's great it tells me my allowable offer and all the tools are helpful!

LLCs are a legal tool, not a tax one.Transfer from personal name to LLC/Due On Sale ClauseIf one is transferring property title from personal name, a Grant/Warranty Deed would be drafted/recorded to transfer title.

The profit was used to buy a higher quality SFH in the same area.