Maybe after 2 years, you'll be ready to start finding your own deals and making things happen:)

If you're buying in Milwaukee, why not get a good PM and buy your own properties?

The idea is to convert a multi-family building into condos; but not in the traditional sense where you separate pre-existing apartments into their own condos; but in a way where you combine the common areas of all of the apartments in that whole building, and turn the individual rooms within those apartments into condos themselves; thus transforming the hallways, kitchens, bathrooms, living rooms, dining rooms, porches, balconies into common areas of the condos. 

I have a confession: my only duplex, which I gave owned now for 2 years and recently moved out of from a house hack, has proven to cost me more to maintain/pay taxes/repair/fix etc to the point where my cash flow is close to zero.

We have secured a home equity loan against our home (which we own out right with no mortgage payment).

Call the PM (I don’t think HABD will provide information on a property you don’t own - even if you can get them to answer the phone).

2) He's owned this outright for a long time and bought it for only $33k.

They are actively managing their properties, do their own recordkeeping at least once per quarter if not more often and are ready to go with reports and back up very quickly at the end of the year. 

While I’m not a newbie, I own two condos as long term rentals, I live overseas and thus my real estate experience is overseas.

I don't have that experience or too much knowledge outside of my own research.