I'm also divided but I would say my mind thinks this is best, as you've seen, it differs from person to person;
Anyway, personally I would (and did to an extent) level your main character in a build that you most wish to play so far as to hit the extra generation experience cap while acquiring the heirlooms that are more specific to the class, so for example, bows due to the requirement to have power draw in a build or your higher strength armour etc. (I do not know for certain if that is still a requirement, I assume it is but I haven't retired for nearly a year and a half.)
Once you have done that, you should have your "staple build" and most of your equipment (15 generations, therefore 15 looms I believe, I never hit the exp cap!) which means that you'll have enough for 5 +3 pieces of equipment.
Then you really have a choice, do you continue your main build, with that equipment through past for a few more generations to utilise your generation bonus to "quickly" acquire some more looms to bolster your armoury or do you allow that character to live on into old age and utilise your generation experience bonus for quicker levels.
If you do continue on building your character, that's where retiring your alts comes in, retiring those really is strongly for when you have your main in a position that you never want to revert back, you've invested too much time into making it. That's the position that I am personally in, I didn't max out my retirement bonus however and I've hit level 34, I traded for the extra loom points and I use an alt to "grind" extra points if I want them although he is only generation 3 (14 generations with 22 heirloom points).
Anyway, there's my personal "best method" given a best case scenario anyway.