There are many attractive suburbs and neighborhoods to invest in throughout Chicagoland but if your intention is to invest in multi-family then you'll find far more inventory in Chicago.

I would recommend starting to look at on-market property in each location to see what the inventory looks like.

While there may be appreciation opportunities in other markets, it seems like the inventory is getting pretty low.Would love to hear what you end up choosing and why, when you do make a decision.

Any informed or educated investor in San Francisco would never let a condo sit vacant because a condo (in most cases) is not subject to rent control as @Yonathan Randolph correctly pointed out.The guidance we have shared with many of our clients during Covid-19 is to be aggressive with the pricing of their condos because of the one two punch of both anemic demand and high inventory in this property type.

DC inventory is at all time historic lows.

I am planning to only live there for 5-7 years and hoping to turn it around and sell it later with a good price.I am nervous that I am buying at the top now as the market has already priced in the low interest rate + low inventory + people want to get out of the city.

Do I see enough inventory down here that would allow you to implement a big acquisitions operation?

Not that it's an excuse for sloppy service, but with such low inventory and bugger-all extra work going into offers, overbidding, etc.... they're just knackered to the bones and can't dedicate the same TLC and focus to clients as before.

If you can buy vacant and screen and place new tenants, you could do just fine since there is little rental inventory available in many markets.  

That is going to continue to put a restriction on inventories into the marketplace.