The realtor actually suggested I go lower.

A better strategy and use of time would be to actually do a STR :).

I guess I’m looking at alternatives options, if this is to hinder me acquiring in the future  

Con's- more expensive monthly, locking us down to CLT/ condo building for what I am guessing at least 5 years to at least make it worth it. not as much revenue/wealth building opportunity as duplex

Actually @Devvrat Kumar they ARE listed in Zillow, etc.

Hmmmm I guess I'm off to the races!

So if we want to buy higher good quality asset where insurance cost is matching with rebuilding cost in Milwaukee, I guess we have to buy something around 400k or min $250 PPSF ? 

I also agree with the other post on comparing actual MLS sales that have ADUs close to your area vs the cost of the addition.

My biggest concerns are - to find a deal and then actually get a cash flow from day one. 

I guess I will have to decide if cash flow or “quality market” is more important for my first deal.