If they are the quality PM you say they are, there is nobody who is going to know more or give it to you straighter then them. 

Part of that you can justify because of the necessary repairs, but overall higher price points appreciate differently.The median home price has basically doubled in Milwaukee from about 160k to 320k in the last 10 years.

Online Facebook groups can be fruitfulOnce you find a property things tend to move fast so have a good contractor available to help you estimate repairs. 

@Tyler Gilpin When you say "does pretty well", is that more of a commentary on the quality of the tenant (aka "lack of damages to your property") or the timeliness of payments (either via HUD or the tenant's portions)?

If a major expense comes about (i.e. roofing repair, hvac, etc) we would split that as well. 

Even with the finishes being better in the class a, I suspect it will have the lower maintenance cap ex due to better quality tenants

I definitely recommend that you seek out a Certified Cost Segregation Professional so that you are confident in the quality of the work performed and the deliverables produced.

Are their listings detailed with good-quality photos?

If selling is on the table, a 1031 exchange could allow you to defer taxes and reinvest in properties with better cash flow or lower maintenance needs.Since repairs are mostly handled, it might be worth reviewing your rents to see if there’s room to increases/ways to improve cash flow.

Are you certain the after repair value will justify this $40,000 budget?