Yes, it absolutely does. Perhaps this is part of the problem. Maybe our FO is looking at our players as material assets and needs to look at them more as human beings.
Whatever your budget is or isn't for Corbin Burnes, the best pitcher in your franchise history has at least earned the right for you to communicate with him and tell him your intention and direction. Can David Stearns or Matt Arnold not carve out some time to sit down with Burnes? Simply say "Hey, Corbin, we appreciate you and would love to discuss your future here. We'd love for you to be here a long time, but we want to be transparent and straightforward about what we can offer you. Because we're forced to be budget conscious in a small market and you're still several years away from free agency, we aren't able to offer anything comparable to the free agent value for your caliber of a player. "
"We'd be happy to buy out the rest of your arbitration years at "X" amount of dollars and tack on two team options of $30M each with $5M dollar buyouts." (or whatever they're comfortable offering, this is just an illustration.)
"If that's a direction you would consider, we'd be happy to discuss it further. If that isn't something you have any interest in, we'd be happy to continue to go year to year with you. Please understand that the time may or may not come when we have to consider trading you prior to losing you in free agency if we feel that the compensation isn't something we can pass up on. Until then, know you're appreciated here."
Simple. Easy. The right thing to do. Keeps the player from a confused look in interviews wondering, "Why haven't they discussed an extension with me?" I don't care who the player is, don't just assume they know they're out of your price range and leave it at that. Communicate.