Here's my second shot at explaining Story Points for estimation in Scrum:
When I switched to points I decided to if I could meet those two points;
1) find and argument that justify the switch and that will convince the team
2) Find an easy method to use it.
Phase 1: Convincing
It took me a lot of reading on the subject but a finally found the argument that convinced me and my team: It’s nearly impossible to find two programmers that will agree on the time a task will take but the same two programmers will almost always agree on which task is the biggest when shown two different tasks.
This is the only skill you need to ‘estimate’ your backlog. Here I use the word ‘estimate’ but at this early stage it’s more like ordering the backlog from tough to easy.
Phase 2: Putting Points in the Backlog
This step is done with the participation of the entire scrum team.
Start dropping the stories one by one in a new spreadsheet while keeping the following order: the biggest story at the top and the smallest at the bottom. Do that until all the stories are in the list.
Now it’s time to put points on those stories. Personally I use the Poker Planning Scale (1/2,1,2,3,5,8,13,20,40,100) so this is what I will use for this example. At the bottom of that list you’ll probably have micro tasks (things that takes 4 hours or less to do). Give to every micro tasks the value of 1/2. Then continue up the list by giving the value 1 (next in the scale) to the stories until it is clear that a story is much bigger (2 instead of 1, so twice bigger). Now using the value '2', continue up the list until you find a story that should clearly have a 3 instead of a 2. Continue this process all the way to the top of the list.
NOTE: Try to keep the vast majority of the points between 1 and 13. The first time you might have a bunch of big stories (20, 40 and 100) and you’ll have to brake them down into chunks smaller or equal to 13.
That is it for the points and the original backlog. If you ever have a new story, compare it to that list to see where it fits (bigger/smaller process) and give it the value of its neighbors.
Phase 3: Velocity & Estimation
To estimate how long it will take you to go through that backlog, do the first sprint planning. Make the total of the points attached to the stories the teams picked and VOILA!, that’s your first velocity measure. You can then divide the total of points in the backlog by that velocity, to know how many sprints will be needed.
That velocity will change and settle in the first 2-3 sprints so it's always good to keep an eye on that value