You had options to get this done early on - whether optimal or not - and you chose a different course.

It doesn’t always have to be about optimizing everything and maximizing returns.

We treat each property as our own investment to optimize the returns of the owner. 

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. 

So by optimizing all your ads they all benefit from each other.