If you are remote, Oakland gives you a lot of inventory with great lifestyle (food, accessibility, etc) and a bette price, but the schools are lackluster (although changing).We did the live-above-tenants thing for a year, and enjoyed it because our tenants were incredible but candidly were ready to move. 

Five minutes into the MLS I found 2 properties in her price range and when she hemmed and hawed at those not being good enough I just put her on an MLS drip, gave her my card, and let her float off into space lol.Sellers are worth more effort up front because they take less effort in contract-to-close and you get some free marketing with the for sale sign. 

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).

You totally rang a bell and I’ll have to certainly go back and investigate.  

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.

As an investment property you can go up to 85 LTV on a portfolio loan with interest rates in the 3.25% - 3.50% range.

Available rental inventory far exceeds demand. 

Are there a wide range of renters there (Class A?

Our inventory has loosened a bit so more buyers are getting into houses.

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