I was under the impression that a player's position can be changed only once during his career. I have a few players that have a position change in their History, but the New Position button is still available (I went as far as the height/weight info but did not confirm the change). Any ideas?

You can change multiple times - there are some limits though (not sure if it is season or career)

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Hartford Attack

That's contrary to the help screen ("Once a position change has been made, it is permanent"), but good to know. It will be interesting to see how that is affected by conversion to the new game.

It's permanent in that if you immediately change the player back to his previous position he won't regain the ratings he had before he switched.

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GM, Atlanta Wolfpack
Formerly of the Anchorage Wolfpack and Huntington Beach Wolfpack and now back as a mediocre GM
CFL Champs - 2026, 2029

Is training camp the best time to make a switch?

Ok, position change tips from someone who really does it too often, to be honest.

Permanent. Yes, the change is permanent as in, it cannot be undone without penalty.

Switching a RDT to a LDT is an easy transition that should barely effect a player at all. But DE to LB is more difficult, and after doing so, deciding to switch back to DE can make just about any player in this edition of FOF useless.

The in game rating for after switch is a complete and utter lie. I had a guy switch and the game showed me 1/8 as his current/potential, but I knew I had to trust my data that made me do the switch to begin with. Once submitted and getting the new file back after the next stage had been simmed, the player had made the switch with a 12/59 cur/pot. On the other side, a guy I switched had the game say 26/32, but after the new file from the sim came, he was a 10/19.

Best time to make a switch? As soon as you are sure you want to make the switch. The switch process almost always results in a loss of experience and current rating, unless you are moving a maxed out vet from LG to RG or LDT to RDT, etc, but even sometimes in those cases. Making the switch as soon as you know this is what you want to do allows the switched player to start gaining experience and raise his current rating in the new position. Letting them get more current in the previous position means they only bring a percentage of that over to them to the new position wasting some of that training time and current rating in the process.