This is making quite a bit of sense. I thought for sure my battery was going bad, but I checked it and it's fully charged, so I think the battery must be ok, because most of the time, the bike fires right up. Only once in a while does it struggle to start.
Also, I have had experience with starters going bad on both cars and bikes, and it's pretty much like you said. It just gets progressively worse. It doesn't work most of the time and then act up once in a while.
My bike struggles to start mostly at fuel stops even in this cooler weather, but if it sits long enough, it starts with no problems. This convinces me that it may be this hydrostatic lock that you're talking about, because if the bike sits for just a little while, then the pressure is there making it hard to start. However, if it sits a lot longer, then maybe the pressure has time to bleed off and it starts easier.
I'm just guessing, but it sure sounds like what my bike is experiencing. No big deal really, because it does always start after no more than 2-3 button pushes and runs great. I'm actually relieved to hear this because I didn't want to have to buy another battery yet.