I have a twofold question for you folks about EP management.
1- Do you always put the caps back on the EPs as you "zoom" from shorter to shorter EP? (i.e. take out the 25mm from the scope, re-cap it, de-cap the 17mm, put it in the scope, focus. Take out the 17mm, re-cap, de-cap the 13mm, put it in the scope, focus, and so on). Or do you de-cap everything, or at least your most used EPs, and keep them so for the observing session?
I take the caps off once and store them in a plastic bag. At the end of the night, I put them back on. How I manage the eyepieces during an observing session depends on the particular telescope as well as the conditions. I frequently observe where it's very dry and not particularly cold. If I am not expecting eye lens fogging or dew, then I am comfortable with the eyepieces stored in a rack or accessory tray.
If I am concerned that the eye lens may fog with my breath or that dew is a possibility, then I store the eyepieces in the case and close the lid each time. My eyepiece case(s) have cutouts and the eyepiece lay flat so their easy to handle. Each eyepiece has it's own place so I don't get mixed up.
In the winter in Canada, I would think that you would need to keep your eyepieces covered when not in the focuser and you may need some heat as well.
2- Do you do this whole progression every time, from 25mm to 17mm, to 13mm, to 8mm, to 6mm, then barlow the 8mm, then barlow the 6mm, or do you skip some steps?
Since I am a star hopper, I generally start out with a low power eyepiece. From there, it depends on the object. If I am viewing a planet or closer double star, I will generally go to a higher magnification, maybe 150x. From there, I will swap eyepieces, increasing the magnification until I find what seems optimal.
Otherwise, it depends on the object. If I am familiar with the object or have a good idea what I should see, I generally jump right to that magnification. If I am using a ~30mm for a finder, low power view, I might jump right to the 13mm or 9mm for a globular cluster or smaller open cluster. I generally have a good idea of what magnification will about right. It also depends on my mood, stepping up in smaller steps is fun and I get many different views of the object.
In your situation, I would tend towards doing the entire progression. This not so much because it would be the most efficient. Rather, you gain experience quickly as to which eyepiece works best for each object as well as a sense of what each eyepiece can do. When you say to yourself, I think the 8mm will be best, then you can make the jump and see how it worked out.
Swapping eyepieces is part of getting the best possible view or views. There's a lot of theory, a lot of analysis one can do to try to determine the best eyepiece for an object but I think it's best to pretty much forget all that and just see what works best for a given object.
So I've been observing the skies for a couple of months now, and I think I finally have my setup down pat, equipment wise. I'm having a lot of fun discovering this hobby (when I can actually go outside).
It does look like you have a nice scopes and a full range of eyepieces, a red dot finder and a 50mm RACI finder.. As they used to say, "Now you're cooking with gas." The red dot finder (or Telrad) plus the 50mm RACI finder is my favorite setup for star hopping.
Now if you can get some more clear skies.