I've been an Eagle user for years. I know it has its warts, but I know my way around them, I'm fast with it and it's served me well. I have the hobbyist license (standard, but cheaper for non-commercial). I've been bumping into the board size limits. I'm still not planning to make any money, but I do want to build bigger boards. There is no "serious hobbyist" license. A "PRO" license is going to cost me $1K+, so before I make that investment for my hobby, I'm trying to evaluate whether I should switch to another solution.
Besides my accumulated knowledge and known-good parts library, the "killer feature" in Eagle for me is really good forward and back annotation between PCB and schematic. My flow is to create an empty schematic and board from the start, open both on my dual head system, and as I place large parts in the schematic (external connectors, mounting holes, major ICs and such), I put them in their places on the PCB. I begin routing when the schematic is close to done, but still go back and forth quite a bit. When I'm done, I'm done. This is a must-have feature for me.
Keeping in mind that the Eagle PRO license is effectively unlimited, should I spend that $1K elsewhere and take the opportunity to move to a (better?) package? All the packages I've looked at are either considerably more expensive, not really very good, or have severe restrictions (pins, layers, board size, etc.) at the ~$1K price point.