Any thoughts on an optimized strategy?

The difference is I don't spend hours trying to convince people and rationalize to myself that these sub-optimal choices are in fact optimal.

Without experience you might think something is a good deal, but a good realtor can point out that this particular properties location is not optimal and hurts its value3.

From all the information The OP has provided, my opinion is that the OP made non optimal decisions at multiple points in their experience. 

The investor has to decide what level of each and mix is optimal for their situation.For example, you might own 4 properties with a sum total of 50k in equity but one of the properties generates $900 per month positive cash flow.

Depending on the skill of the technician, you can actually end up spending up to a day just redoing the plumbing to optimize the way the systems work. 

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This is important not only from the point of view of design - different types of indoor units allow you to create the most optimal distribution of cooled air in rooms of a specific shape and purpose.

This sounds like the kind of value add play where you need to clear the building to optimize the assets performance.

From my (personal) perspective you have a situation that demands pessimism so you can't afford to interject optimism.