It may work as a complementary strategy in which I can slowly improve my primary residence, buying slightly larger each time and renting the properties I move out of, but my concern is that if I'm intentionally selecting nicer houses for myself, will I leave a trail of negative cash flow behind me?

For those homes, so much needed to be done with them that I did not check into low-e or argon gas because at the time I knew that the double pane & vinyl would still be an improvement of energy performance compared to what they had at the time.

@Christian RojmarGoogle irs definitions of improvement vs repairs.

If they improve the sites functions then I’m ok with the fee.  

Putting more down obviously improves your cash flow, but minimizes the money available to property #2. 

As a general rule, if you do work to improve the building it increases the assessed value.But the amount could be negligible in the end and there could be a delay of a year or more until it affects the assessment/taxes.For example, if the assessed value increased by $10,000, taking into account the 40% discount on assessed value for owner occupants and applying the tax rate of 24.56, would only result in $147 more tax per year.

The area is improving and we wanted to help Columbus improve the downtown areasHow did you find this deal and how did you negotiate it?

Historically 10 years after purchase the cash flow situation is much improved from the initial cash flow.  

The only amount abated is the improvements made

Many have guidelines for improvements especially basement finishes.