@Jordan Smith
My reasons behind preferring duplexes is mainly due to availability and cash flow. 4 unit buildings have been hard to come by, and anyone in a decent area is hard to find for a reasonable price compared to duplexes. 4 units between 200-250k need a lot of work or in non so great areas. If a nice 4 unit pops up it tends to be around 350-400k. Rents might be 800-950 per unit at that price point.
Now, if I had the option between a 400k 4 unit that rents for $3.6-3.8k/mo VS two 200k duplexes that can rent for between $1050-1250k per unit (both my duplexes rent for $1237.50 when averaged out, and were purchased for 185k and 189k in same neighborhood). I’d take the duplexes because more rent potential, easier to rent, less tenants complaining about each other, easier to sell, less turnover as it feels more like a home than smaller apartment, and various other personal reasons.
As far as where to house hack, like you, me and the GF are in same position. kidless and enjoying going out somewhat often still. I settled on an area called Nash Park as its close to Wauwatosa which has its own nightlife, downtown, trails and parks and only a 15 min drive from DT MKE. It was a bit cheaper than Washington Heights which has soared past 4 years.
But if I had to pick areas near all the cool bars, restaurants, parks and other fun things I’d go with any of the following: Bayview, Lower East Side, River West, Walkers Point, Washington Heights, Wauwatosa near North Ave or its Downtown, West Allis. And none in a particular order.
If you do want to get a little more cash flow and prices that aren’t mid 250k+, West Allis, Kops Park, Nash Park, Enderis Park is a nice west side area to look close to Tosa.