Thanks so much @DomainRecap ! Wow those are some great names at the top of your list!
I think IND is an incredible name, either as shorthand for independent (i.e. indie music or books) or as a three letter acronym with various possibilities like intelligent, international, interactive, etc. at start.
I also like repost a lot, for the reasons you say. I don't quite visualize the business, but there is so much use in social media, I am sure those more creative than me will see use.
On your word list, wealthiest strikes me as a very strong word in the financial planning and investing and estate management areas, or a great name for a financial website or magazine.
I had some trouble ranking some of the names, such as Flavor.ca (the US spelling, but still a great word) and as you mentioned, Wealthiest.ca. That was a tough one, as it sounds great, but you also have to take into consideration Wealth.ca and Wealthy.ca, both of which are superior single-word domains IMO.