I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.

Better to have half a dozen high end paid for props that take very little work and not so much drama..

Some people will say, "Take out a quality Insurance Policy and you will be protected."

In New Jersey, there are numerous brokerages to chose from, and I highly suggest you do a google search and look into 100% virtual real estate brokerages in New Jersey. 

Since you're analytic savvy, run some high level amortization schedule scenarios to see how much equity you gain through annual principal payments.

And if it's a high amount, would you be better off just using that as a downpayment and get a standard new investment loan?

Mainly because of increased competition coupled with high interest rates.  

The risk to my business is much too high just so the agent can make a little more money on the transaction. 

The owner said he would sell but at a very high price.

You cannot have a contract that simply states "install high-quality countertops" without specifying the quantity, location, type, or style.