I wish I could rely more on the tea fairie and the "just know" but with most teas I rely on my tools to guide me.
With oolongs It seems I can't go wrong no matter how I brew them. They are always soo delicious.
There are four teas I can think of off hand that I use sight to kind of judge when there done and thats; long jing, Jiu Hua fo cha, ding gu da fang and silver needles and I think thats because I have more experience brewing these than any others. I brew them all for about a minute but will either stop the infusion early or let them go a bit longer based on the color of the brew. Usually I stop the fo cha early because its more floral and let the long jing and ding gu da fang brew longer to bring out a stronger nutty taste.
Oh no! Hang in there, it'll get better. I was on the couch for most of a week when I had mine out; lots of smoothies/milkshakes helped - have you thought about a tea smoothie? I have a powdered green tea I use for smoothies (and cheesecake!) which works well. Or, I brewed extra-strong tea once, froze it, stuck it in the blender with some simple syrup and churned out "italian ice"... but tea-flavored!
