My goal is to transition into the principal side of investing as quickly as possible and do something similar to you with out of state investing.Frankly, it feels like I’ve absorbed a ton of knowledge yet I’m still missing the guidance/mentorship to take that first leap of faith.

But they will definitely count the $1,500/month you are paying on principal and interest as debt when they figure you DTI.SO with all this said using OPM like @William F.

The cash flow is there to cover the interest and principal on the HELCO so the added cashflow from having another property would grow my bottomline overall I believe (please tell me if Im wrong). 

Do not also forget moving out now gives you principal paydown thus increasing equity.

Here's a blurb from the IL Gov website:This annual exemption is available for residential property that is occupied by its owner or owners as his or their principal dwelling place, or that is a leasehold interest on which a single family residence is situated, which is occupied as a residence by a person who has an ownership interest therein, legal or equitable or as a lessee, and on which the person is liable for the payment of property taxes. (35 ILCS 200/15-175) The amount of exemption is the increase in the current year's equalized assessed value (EAV), above the 1977 EAV, up to a maximum of $10,000 in Cook County and $6,000 in all other counties.

Purchase price of property at 5 years is calculated at (Current Property Value - Option Payment - Principal Portion of Lease Payments).Over the 5 year lease the buyer takes on 100% of maintenance costs, improvement costs, taxes, and insurance. 

Can you explain principal and how do I pay it down faster.

I tried running some numbers on the properties I own, and all of them I couldn't afford the principal + interest on down payment as it completely wiped away my cash flow.

In addition to principal paydown and appreciation (crazy hot market in Denver) make house hacking attractive from an RIO and saving perspective. 2.

Your principal does not decrease and continues to grow and should almost always outpace the interest you pay on the liquidity.