Cleveland is definitely a good cashflow market but depending on what your goals are for real estate, you might end up sacrificing some appreciation in the long run.

Need to convince the family that sacrificing a garage to gain an apartment would add to the property’s value, not diminish it.Long version: We have a 2-car garage with a 300sq ft bonus room above it.

This is impressive as typically in my experience higher wage earners or white color jobs do not want to mess with the short term hassle of househacking but sounds like you were on a mission and sacrificed short-term pain for long-term gain.

You could house hack if you are worried about capital expenditure for acquisition but that also comes with smaller inventory (multifamily or homes with ADU's) or sacrificing of current lifestyle (rent by the room).

Is the industry knowledge gained from a RE profession (RE agent, Project management, property management) worth sacrificing for a more lucrative but unrelated line of work?

Next thing you know you walk out with 4 clients and transactions for sacrificing 1, because you swallowed your ego, focused on learning and growing, results vs being "right". 

With a good property manager, you benefit from your investment without sacrificing your time and health.5 – You don’t understand the laws.

So is sacrificing for big things. 

If you don't want to maximize your return and can still break even then buy what you like regardless if it would not appeal to as many people.I suppose I didn't express this directly or succinctly but yes, I am okay sacrificing some immediate cashflow by not focusing on what appeals to the masses. 

Looking to minimize costs without sacrificing quality to improve ROI.