@David De La Torre great anwers so far!

Ever wonder why some investors keep scaling… while others stall after their second deal?
It’s not just about finding good properties —
it’s about how you fund them.
The structure of your capital stack determines ho...

My holding company is in Dover Delaware,  I will be opening an LLC in Philadelphia pa as well.  

This often follows a 1031 exchange, where the investor first trades into a Delaware Statutory Trust (DST), which is then contributed to the REIT under Section 721 of the tax code.There are 8 public REITs that have mature 1031-721 strategies, and a fiduciary due diligence obligation requires deep financial analysis of each REIT.I’ll refer you to this post to learn more >https://www.biggerpockets.com/topics/1217983

If you can, test ONE unit in the market before diving into an entire village.Not saying you shouldn’t do the full community, but a single proof-of-concept install will tell you more than any spreadsheet ever will.You’ll learn:• how the city reacts• what permitting looks like• whether inspectors push back• how neighbors respond• whether appraisers understand it• how tenants perceive it in your marketThat small test can de-risk the whole project.2.

It becomes a de facto taking.There’s also an important human and economic dimension: The owner actually uses the land to operate a truck fleet, which is how they work and employ others. 

DO NOT get expensive appliances or fancy tile or marble counters...all of that doesn't matter and will de destroyed over time.   

Paul De Luca I already work with a Dionne Branch from EXP Realty.

The property sits at the bottom of a cul-de-sac and gets runoff from the road and nearby lots.

I like @Paul De Luca recommendation for option 2 because of the DTI situation and your overall goal of buying the next property.Either way, I don't think you can go wrong with either of those awesome Chicago neighborhoods, unless one is much closer or further away to the blue line - that could really help with your appreciation and long-term value!