So, find comparable units and figure out how long they sit on the market.

Check Airbnb and compare your potential STR to the listed rentals and get an idea of your location and price point. 

I'd compare coverages and narrow down from there based on what you want and can get.  

I started looking OOS to other recommended markets but realized prices in my market are still relatively low when compared to other areas, meaning in the $225,000-$325,000 range for 3-4 units but there’s not much inventory.

It's like musical chairs and this will keep driving prices until the market finds an equillibirium between supply and demand, which all free markets will do over time, but since supply and demand are not that flexible it has to be price that will reduce demand until we are balanced.Milwaukee is also seeing a little bit of an increase in imigration due to climate change: smoke, fires, drought, hurricanes, floods, fresh water - in combination with remote work and low cost of housing compared to most of the country.

Before visiting the property we did our due diligence by looking for comparable properties on the MLS in order to understand if this was a good deal.Determining our offer price:We use the 70% rule to determine our offer price on any property.

You can also do some secret shopping by pretending to be a renter and touring homes on the market that are comparable to yours. 

You might want to follow the "Deep Dive" series we're doing on our BiggerPockets blog about Metro Detroit cities, City of Detroit Neighborhoods and comparing Metro Detroit to other hotspot cities investors usually consider:https://www.biggerpockets.com/...

When I was offered transfer from GA it was to DC area, Northern VA is so expensive compared to GA that we turned down transfer, company came back and said we could live in Richmond area.

The tenant mistakes and contractor mistakes are nothing compared to not being 2 years closer to my goals.