I am in the same general area of the world. I watch the different weather channels and deduct for elevation. I do not use the Frogg Toggs in winter. I use a little more substantial rain suit - Patagonia Rain Shadow jacket, Marmot Precip pant. I got some of the nylon layers that Walmart started carrying - I think the fabric is called Revert??Revent?? drimore??Athletic works, maybe?? Anyways, it works fantastically. There are four different thickness and I have one of each - they go in rotation depending on expected temps. The best peice is a Patagonia micro puff vest. I retired two down vests and ended up with this - and would never go back. I have a North Face down jacket that also comes into play if its gonna be unforgivingly cold.
Walmart did sell a two layer - wool/polypro top and bottom, but they quit carrying it. I have two sets left. These are super versatile. They are available at Gander for two or three times what I paid a few years back.
In camp I always have my camp clothes that I do not hike in, unless I have to. They stay dry. Fire is always a plus. If I am going to have fire, I leave my hiking clothes on until the after camp is set then I dry them by the fire before changing into camp clothes.
I used to jump in the sleeping bag too soon because I got cold. But once you get in the bag it is hard to get back out - so I stay active in camp. I might build a fire, or throw on the headlamp and go for a little hike up the trail. I prep my lunch and whatever for the next day. Basically I keep moving until I'm ready to read and sleep.
I used to go with hiking partners and we would stay up by the fire and talk until late, but mostly I hike alone these days and unless I stay busy I get bored and end up in the bag too early.
Another thing I do is plan my camps accordingly. If I am going to Mount Sterling, where the wind always blows, I know I will have a heavy pack full of warm clothes and a tent. But if I want to carry a lighter pack I stay low.
And one thing for sure is that the first day out is always the coldest - it takes me a day to adjust to being away from a heated house/office/car.