As @Dan H. has stated building and ADU can take a while to pay off and could affect the appreciation on the exit sale without a garage which could limit your sales to another investor. 

Limited capital means that partnerships will help us move faster while the environment is profitable.

I have learned that in today's world of information you do not need to limit your investment to just markets you live in or normally travel to. 

So in the words of Clint Eastwood: "A man has to know his own limitations."

The problem with southern Wisconsin is that we don't have reliable snow coverage anymore, so you are limited to the summer season and will sit vacant for the winter.

In PA statue of limitations is 2 years

A rider allowing for using your owner-occupied property as a short-term rental for a specific/limited amount of time is very different than an investment property being used as a short or long term rental 100% of the time.Also, telling your home insurance company that you STR your home occasionally does not give you extra coverage for those types of risks, it simply means if your renter burns your home down the insurance company isn't going to immediately deny your claim. 

Zoning also seems to be a problem (see below)3. buy a SFH under ARV; live-in renovate => rent => move to a new primary => eventually refinance to pull value out It seems the multi-family options are extremely limited or nonexistent in this area.

Recent discussions in Bloomberg and the Yale Law Journal shed light on the challenges posed by traditional zoning regulations and offer insights into potential reforms that could benefit co-living arrangements.Zoning Laws and the Definition of FamilyTraditional zoning laws often define "family" in narrow terms, typically limiting residential occupancy to individuals related by blood, marriage, or adoption.

One thing to note when getting conventional mortgages and spouses.There is a 10 limit per person for conventional financing.You can either do 10 conventional in each person's name which would be 20 mortgages for 2 people or if you do the mortgages jointly, will only allow 10 in total.My thoughts are not to own joint assets until you are both married.