bought me a new truck, and now i have tons of questions lol

[Adam4pt6]

so 1st things 1st, im pretty new to the forum, and have spend the last couple of weeks just reading countless threads and learning what i can. a little back ground on me, i went to college for automotive work, and spent about 5 or 6 years working in a typical mom and pop shop, aswell as doing cyl heads at a machine shop. I decided that this is a much more enjoyable hobby then career, so now i just work on things on my own time. most of what ive messed with, besides typical maintenance work, has been mustangs and camaros, always geared towards the 1/4 mile, and newer trucks and jeeps for the off road environment. This is my first "classic" truck.

I picked up a 1969 c20, its a 4 speed with the straight six. body is fine, minimal rust(none that needs to be dealt with any time soon), and starts/drives/runs great. the goal here is to have a truck i can drive on a regular basis, but also a weekend project. so far it seems like it will fit the bill perfectly.

now on to my questions. and yes i have searched, and am continuing to search for these answers aswell.
1. who are you guys using for insurance? i put in for a quote with haggarty, they were recommended by my regular insurance company.
2. is it possible to swap this rear to a 5 lug set up? i believe i have the eaton rear.
3. do they make 8 lug front disc conversions? or are there trucks i should look to buy parts for that will work? also, on this note, say i pick up a conversion kit from one of the big companies, what do i do about swapping pads later in life? do they tell you what make/model to buy pads for? do i have to go through them?
4. power breaks... worth it? what do you guys think? and aside from trying to find a kit of some sort what parts do i need? just the bracket, brake booster and master cyl and a new prop valve? this one is still a new topic to me, so im still doing some research.
5. power steering? whats your guys' take on it? is it worth it? my manual steering box has a ton of play in it and will need to be replaced asap... would it just make more sense to switch to power steering? and again, are there kits out there? or a certain truck i should look to source parts from?
6. the plan is to drop the truck quite a bit... right now im thinking either 4/6 or 5/7. its a coil set up in the rear, and ive done a good bit of looking into this, so i dont really have many questions pertaining to the suspension itself, but what i am wondering is what size wheel/tire should i look at? i hate the wheels on it and want to switch them out pretty soon. but back spacing, diameter, etc etc etc im not sure what fits correctly on these trucks.

so theres my entire novel for yall to read, if youve made it this far thank you for taking the time to read all of this and thanks for any of your advice!

im getting an error what i try to upload pictures, if anyone wants to give me the run down on how to get pictures up ill post some of the truck