Even though you’re not fond of DSCR loans, it might serve as a bridge to free up your line of credit for quicker flip-and-reno opportunities.I remember years ago, a close friend of mine was in a nearly identical situation.. from what I read in Forbes, he ended up with zero wiggle room each month.

The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

I’m getting ready to make my next move in 2025 and I’m contemplating on staying here and buying a multi family property as an investment out of state (only an hour away) which would be a lot less capital and have a lot more land lord friendly laws or buy another multifamily as a primary residence locally and hack that property I’m single and live alone.

High LTV purchased at retail (off mls) has large initial negative cash flow- regulations are tenant friendly.  

My initial interest in out-of-state investing stems from the high cost of multifamily properties in New York and the state’s renter-friendly laws.

There may be some lenders that might be a little more "borrower friendly", but I haven't found them (nor do I have the time to look for them).You might be able get better terms if you "house hack" by getting an FHA loan, but I don't generally work with those loans.

Everyone says to find properties and build a buyer's list, but neither matter if you can't calculate the repair costs and also get access to a friend or colleague who has MLS so you can do a proper and real ARV (the other part where all wholesalers fail).

I have always been fascinated with Peoria, though I’m not sure how investor friendly Illinois is.

it is not user friendly at all. 

House hacking will be your best friend starting out .