The one I am used to using provides cost estimates of various rehab products based on specs about the house.

Is not only how much you paid,  you need to pay right base on you resources.Find a good realtor that knows the market.good luckLuis Maqueira MMP

I say “currently” because there is a bill passing through the legislature even as we speak to remove that requirement for 3-4 unit properties, so patience might be rewarded.And just make sure the zoning allows 3-families before you make a decision based on that potential.  

My name is Rebecca and my husband and I have own Captain Save a Home LLC and also run Brew City REI Club, Brew City REI Training Cafe and Wisconsin Contractor and Handyman Club based out of Milwaukee, WI for the past decade. 

There are lots of deals to be had at each meeting.There is another one based off of the FB group Metro Detroit Real Estate Investors which meets on the 3rd Thursday of each month at Mcveighs Pub in Troy from about 6-10. 

Areas that have been good 30 or 50 years ago are still good today.One wildcard though.The city of MKE has initiated a projected called GrowMilwaukee, which is based on the majors vision to increase population (for fiscal reasons, more people per square mile) and they have identified the lack of midrise mixed use districts - they call it the "missing middle".

By understanding and correctly calculating the numbers, finding the right properties, and building a strong team, you can successfully execute this strategy and grow your real estate portfolio.Good luck with your investing journey!

On paper what you're describing might sound doable - but it sounds like your perspective on REI is based off of knowledge of only the "good parts" Managing and owning rentals (yes, even with a PM & price point of sub $50k) comes with its own challenges and headaches. 

I have been a HOA board member and have to strongly agree its best to stay clear of HOA communities that have HOA docs/rules that clearly prohibit STR.

It's not that difficult to navigate through based on my experiences with my clients, easy to use and setup.