1. Try the Kryptonite U-Locks, get a newer one that DOESNT have a cylindrical key, and you can get bike coverage **** where if youre bike is stolen while using their lock, they replace the bike like up to a couple thousand bucks
2. it has to do with your rim size too and frame and fork size as to what size tire you can use, but for road bike, 700c is what you usually use, most are 700x25 and when it comes to potholes and such, look for a slighly wider tire if you can, not too wide of course, and get a durable tire such as armadillos or the gator skin **** by continental
3. i honestly didnt feel much of a difference with disk brakes when i test rode a bike with them, just get some good brakes and just try to have a knowledge of an average distance it takes you to stop, and when its wet just keep that in mind and double the distance and brake sooner just like if you were driving
4. if there is a sidewalk use it if you feel safer, if not, stay as far to the side as you safely can, and slowly work on increasing the speed you feel safe at... you may want to also look into seeing if there are streets parallel to it that have less traffic and try using them
5. depending on your standover height, i would suggest a 56-58cm frame
6.i use a backpack, its a must to have another shirt with you though, even when its cold your back gets sweaty... you could also try a basket either on the front or rear, or try paniers, you may not like the look but if you have to carry 20 to 30 pounds, and dont want a stiff back its a good choice...
7. I preffer drop bars... I used to use flat, and when i switched it didn't feel right at first, but the more I used them the more I liked it... With alot of drop bars you can hold on just like with flat bars, AND you can still change hand positions... I usually keep my hands similar to how you would on flat bars on mine while riding straight and a little slower, and when i have to ride faster, brake, or go uphil put my hands on the lower parts and lean forward a little...