Definitely need to increase water intake. I have been averaging 2 L per day.
Does you doc have you on any diabetes meds?
Metformin, perhaps?

The urine testing helps, but unfortunately to get an accurate instantaneous Blood sugar, you will need to use that pricker.
I hate the thing, but I also have the need to know what is going on. There are some that you can use on other areas beside finger tips which are a bit more comfortable.
As for finger sticking, become ambidextrous and prick a different finger and different hand each time. It gets easier. Use those alcohol wipes, too. The stuff you pick up during the day on you skin and even sweat can affect your readings by 20 points or more.
First thing in the morning will tell you how your overall system is doing. Amazingly, even 30 minutes in the morning can make a big difference, because when you wake, your system starts cranking out glucose to get you going. I can have 68 to 98 right after waking, and 30 minutes later it is up to 130-140.