A drive-to vacation, where the biggest expense is the STR rental, is going to be preferred by many.  

Yes, there is lots of risk and huge downside.

Oscar, often the biggest mistake new investors make is wanting to know everything before doing anything. 

My biggest fear is finishing step #1, and then failing on step #2 due to some random rule I am not aware of, and having sacrificed two garages for an addition, with no possibility for an ADU.Appreciate any insights or perspectives.

Here is a breakdown in my market D-18+%(biggest headaches typically) , C 11-17% B 7-10%. 

Don't always focus on the highest yield or the biggest discount.

Detroit Michigan is without a doubt the number one city in the country for positive cash flow, best rent to value ratio and biggest bang for your investor buck!

I do not see much downside especially if your investing in a primary that you will have a roommate. 

Out of curiosity, what has been your biggest rehab cost to date?

When I first started out my biggest issues with my agents were that they just simply wanted to make the deal and close.