As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

When contract is about to reach 5 years, i plan to make some upgrades on the property and ask for re-finance, hopefully pull out some equity and get a fixed rate mortgage.Let me recommend a backup with emergency fund (equivalent to 24 months operating costs).

Also, I really wanted the units to be up to my standard, but I think I spent more on them making them look better with upgrades, etc, than I needed to.

These upgrades revitalized the home, boosting its curb appeal and market value.

I am looking for insights from anyone who has recently upgraded their electric service in Chicago.

I'm unclear what you mean by upgrading your accounting for the syndication.We use multifamily property management software.

I am an ambitious DIYer and have upgraded every part of my personal home in some capacity. 

We will upgrade it to a Premier account once you’re set up!

We do some cosmetic improvements to bring homes to our standard, typically carpet and paint, upgrade lighting etc.

I got a very good price on the building (about $25k per door), but it was a ton of work as in addition to tenant issues, there was TONS of physical distress (foundation repairs, sewer line and water line repairs, electrical upgrades, new roof, and apartment renovations needed for all units).