Did the funding from all those projects go directly to hire a financial planner? Did this financial planner convince the once open source minded individuals from Drupal to milk the community that has helped make Drupal what it is today?

The posts you referenced on drupal.org are posted by Kieran Lal who is on the Board of Directors of the Drupal Association. He is in charge of fundraising. He's not getting paid for his efforts and he is a long time contributor to the Drupal project. The Board of Directors of the Association is charged with the responsibility of supporting Drupal as it grows. This involves investing thousands of dollars into hosting equipment, defending the Drupal trademark, and sponsoring Drupal related events. By posting on Drupal.org and asking people to take a survey the Association is doing its best to involve the community in making decisions. These issues and more are being discussed thoroughly on Drupal.org where people can post comments, unlike this site.

Your criticism seems to imply that Drupal should exist in a money-free zone. This is an unrealistic and naive sentiment. A huge portion of the code that you use when you run Drupal was paid for with large sums of money by clients who use Drupal and hire Drupal developers. Hosting the Drupal.org infrastructure costs thousands a month. Organizing events also costs thousands and weeks upon weeks of efforts from volunteers. Scaling all of this to accommodate growth over the next five years will be expensive. If you want to see Drupal handle its fundraising efforts well, please participate in the conversation on Drupal.org. Posting as an island on this site doesn't help very much, especially when you discourage discussion by not allowing comments.