This led me to a pseudo driving for dollars style – I would go to showings on the MLS and would see other Multi-family houses next to the property and wonder if they would be willing to sell.

Ground floor is a great pm, there are other good ones also but it depends on your style of investing and goals.

Just know the pros of cons of each, and choose the one that fits your investment style and goals.Best of luck!

Well, as a Boglehead, a house hack would suit the style ;)West Haven and East Haven are not bad, but have pockets.

that changes the answer completely.I'd need to know more about your operational style and goals.  

Also appreciate your attitude about being willing to let a deal go if it doesn't fit your style.

I always spend the money for these professionals:Real Estate Agent - They will help you understand the market when it comes to trends in both prices and styling. 

This is done in Chicago loft style apartments all the time.

but your place need to operate first and you need to show them that your place is making money.Third, you need to decorate your place with a style like you would normally stage a home before selling.

The carpet is an outdated style, and it is getting worn at the transition pieces.