Both of your regular flights are under 3 hours. How quickly does your battery die?
Yes you do deserve a working outlet when one is advertised and FAs that regularly check the cabin. The babies, baggage problems & delays are part of traveling. Hitting the call button is fine if you need service. Don't do it for every little thing but you can ask for what you need if the FAs aren't being attentive.
When you have a problem, report it on board and via the website comments section. I wouldn't go after compensation but if you report what is wrong it gives the company the opportunity to correct the issue. Same for good service. Commend those that do good work to reinforce it and hopefully have it spread through the culture.
There are other options on the MCO-ORD route but I think you're getting the best bet on UAs 737s.