As for boots, try on as many as you can and find the pair that fit best.
This!
I am probably noob-ier than you are, but I did do quite a bit of research on boots, and everything I read said that 1.) boots are the most important part of your set-up, and 2.) try a ton on to see what you like and what is most comfortable to you. There are a lot of fit guides online, and they all seemed to say that you want the boot to be more on the snug side. I think I ended up trying on about 10 pairs before I ended up with mine (Ride Sage BOA).
I went to three different stores and also ordered a pair online (that I ended up returning). I tried different brands, different lace styles, and different firmness. I quickly learned what I liked and didn't like, and what I need. Like I figured out that I need a certain type of boot for my high arches AND something that comes up a little higher on my calf because some styles hit me right in the middle of the calf which I found to be uncomfortable. I learned all of that just by trying them on and walking around the stores, so maybe you'll learn different things that you like or need, too. Some boots were instantly uncomfortable, others were uncomfortable after 10 minutes. The Ride boots were never uncomfortable, though my toes touched the front (which is apparently what you want), so I went with those. So far so good, although I've only worn them twice.
Do you have stores local to you where you can go try on boots? If so, go when you have some time to spend.
Wear the socks you plan to ride in and plan to be patient and just try on a LOT of boots.
