A couple things:
I always park in first gear, but I start the engine in neutral. So my process is: sidestand up, turn the key, pop it into neutral, start the engine (with turning the kill switch on at some point in there).
If you’re doing an emergency stop, don’t worry about shifting, worry about getting stopped safely. You’ve got the right idea there.
A general rule for shifting is that the longer you wait before shifting (letting the rpms get up there), the faster you accelerate. On a relaxed ride, which is basically all I do, I end up keeping the revs pretty low.
For boots, any type of boot will be better than running shoes. Running shoes offer basically no protection at all. If you have work boots or hiking boots or any type of boot, use those. Motorcycle boots are the best, but until then see if you can use something better than running shoes. Also make sure your laces aren’t in the way. Tuck them under themselves, or into you shoe. You definitely don’t want to show up at a stop and not be able to get a foot down.
For motorcycle boots, I have the Tour Master Solution boots, and I’m happy with them. You might want to check them out. (http://www.tourmaster.com/xcart/catalog/Solution-WP-Road-Boot-p-82_7.html)
For pants, I have the jeans with kevlar/cordura lining, and I have some armor that I can wear under them. I also have some real riding pants with armor on order, and they can zip in with my jacket.
I don’t think that feeling scared is a necessity for learning to ride. A healthy respect for the activity, and for the machine that you’re on are definitely good things, but it’s possible for fear to get in the way. Just make sure to stay within your skill level.