The market is increasing, but you can find quality duplexes for under $150k in C+ neighborhoods with quality tenants.

Put more focus on quality over quantity.

From my understanding it comes from the NOI but I guess you could bring in extra in the beginning to speed up the process?

Materials, quality of paint job, quality of paint.

I was going to suggest that but it would take qualifying for a construction loan and most important, finding a quality reliable GC.

I understand condos in downtown are generally a bad investment, but I really don’t want my quality of life to suffer by moving far just for the sake of home ownership. 

Thanks to my high W2 income and not having any debt, it would also be easy to get approved for some cheap 2.x% financing.Having never owned real estate, a good way to get started would be by owning my primary residence for a while, with the intent of eventually renting it out in a few years and in the meantime seeing how I feel about maintenance and home ownership in general.Unfortunately, the areas I am looking at are in very high demand (River North, West Loop, Fulton Market), and have prices such that I would at best barely break even with rent after taking into account HOA and taxes ($300k-500k range for 1-2 bd, HOA in the ~$500/mo).I understand condos in downtown are generally a bad investment, but I really don’t want my quality of life to suffer by moving far just for the sake of home ownership.

I would love to hear recommendations on quality contractors you've worked with in the area. 

I (and many others) have talked about syndications on this forum and there is plenty of 'education' out there to get up to speed.

We are mid-stream through a value add process which will enhance the quality of life for our residents and increase the value of our asset through unit upgrades, common area and amenity enhancements, and ultimately rent increases.