Originally Posted by
AJ_Daubz
I currently have around 8 hours....the forecast looks marginal with fairly low clouds, possible drizzle and strong winds...I'm just wondering how long it usually takes to get comfortable with this kind of thing?
The rest of one's life? A better question is 'when will I be safe with this kind of thing.' It seems that for the first 500-1000 hours it's best to pay respect to any sense of unease about a situation:

From
Predicting Accident Rates From General Aviation Pilot Total Flight Hours (FAA doc).
I don't know if this was covered in your training, but accident statistics demonstrate a Dunning-Kruger type relationship, where the risk of a serious accident
increases for the first few hundred hours, before then decreasing. So, confidence early on is not per se what you want, instead incremental increases in experience with no hesitancy to drop back a few notches if feeling out of your element.
With your desire to do a lot of cross-country flying in the future, a rule I was taught is that GA flying and schedules do not mix. You have to be willing and able to park somewhere until conditions improve. The flight you describe doesn't sound like an enjoyable one to me.