Yes, a little awkward for my son but he had become accustomed to talking to adults/coaches during this process. We always made sure he was the mouthpiece to the college coaches. My son grew up a lot during his recruitment because he quickly realized that Mom & Dad were only going to provide guidance. I had no problem talking to FA office as I had talked to them a handful of times previously.
So, I should have clarified in Situation#2, College#2 was my son's preference due to their engineering program. He had stack ranked 4 colleges based on his weightings. We were pretty sure College#2 was going to financially match College#1, as College#2 had recently posted a matching FA policy (for colleges in their conference) on their website. The (additional) $4k yearly merit award was a total surprise to us...we didn't ask any questions. ;-)