I have a rental in Prairie Village on a cinder block foundation that is having issues with standing water in the basement (unfinished) after heavy rains. 

:)  I use to live in Smyrna near market village.

Push east towards Charles Village, Station North, and Old Goucher and you can get a better deal.

My wife and I bought our first place in 2017 in Merion Village - a revitalizing neighborhood in South Columbus.

@Meryl McElwain I've had my tenants in logan square and Ukranjan Village pay on time throughout the pandemic.

In my opinion, it's very subjective as it's really up to an individual's immediate and future goals, their risk tolerance, their experience and their resources....neighborhoods are also subjective---I personally like areas where I can get SFRs for less than 60k and duplexes for <80k and that's going to generally be northside/northwest Milwaukee and south side Milwaukee like 53204, 53215 or Clarke's Square, Lincoln Village.....but pricier areas such as Bay View, Cudahy, South Milwaukee are extremely popular as well....also, where you start isn't always where you finish--many people start on the northside because you can get 4 properties for 100k vs 1 property for 100k and then they move in to better, more passive areas.

I have a small multin Charles Village I got on va. 

These zones claim to be for "stimulating growth in depressed areas" and many of these areas do indeed fit that category, but areas of Bucktown, Avondale, North Center, Roscoe Village and Ravenswood all qualify so don't dismiss your property because you feel you are in an A or B area.

Also, because this was a nicer rental home with premium rent prices, I had a drone video made of the surrounding village area and how my home fits in.

I'm currently in this process while deployed in the middle east but I'm from Greenwich, should be back in a few months.