Questions for the experienced bfers

I'm 12 weeks in, for a few weeks it got easy and I thought wow, this is what they mean when they say it gets better. But now it's hard again 😂

1. My boobs are soft now, never feel full and I don't leak anymore. Does this mean my supply regulated? Did you experience a drop in supply when this happens? Little one is attached me to for hours in the evening / night (night I think is for comfort) but I really think I have no milk in the evening for her 😭 what do I dooooo

2. She won't feed in certain positions now, some days the only way I can get her her to latch is side lying. This will make going outside impossible 😅 do they eventually get over this? Can I do anything different to help her feed in the usual position