I didn't dry up, I did get sore boobs on and off.. I never tried fennel tea, although eating it did help, so keep it up unless it's vomitus
My DS, unfortunately not like yours! Has never been into food to the point of taking everything offered lol so if he seemed hungry I just gave him another half bottle, I must say though I stored and fed DS my milk in 100ml amounts so there was as little wastage as possible... I hope yours doesn't guzzle you out of house and home if you try the give him what he'll take approach though, as long as his weight is rising in a nice steady curve then he's fine - it's probably best to keep an eye on the weight, if only for your sanity!
I'd say optimum pumping time is 20 minutes for each breast, obviously if both at once then that's only 20 minutes... the longer you do it though the more stimulated they will be... and the more you cut down on the amount of times a day you pump the more time you should add on, I'd add on 10 minutes per breast for every pump you drop (when you feel comfortable enough to drop pumps that is, which may not happen for some time!)
Your night thing sounds perfect, you're doing brilliantly, you will make it to 6 months you're being so brill even putting yourself through this for him, if you ever find it too much and really feel like you have to give up, don't feel guilty... most mums never even try this, and for good bloomin reason!