1- don't know...
2- yes, I'm pretty sure that's how it's supposed to work- two licenses.
3- as long as hidden players are on, scouting nations can be very rewarding if you scout the top baseball countries- so rewarding that it makes the game too easy, I find. It's definitely fun, though. If you're interested in data, I ran some extended experiments using the next-to-last patch (it's possible this aspect of the game has been tweaked in the last patch or in OOTP8), and wrote up the results here; there's lots of great data from redsoxford there as well (warning- a long thread!):
http://www.ootpdevelopments.com/boar...d.php?t=151652
The summary- in Excellent nations, a scout will find roughly one player every 4 months. The number found, and the quality found, drops off as the quality of the baseball program goes down. A country's population, and the scout's ratings, don't seem to matter at all. There's not much point, from a baseball point of view, to scouting weak countries; the players you find won't be worth anything.
If hidden players are off, you'll find nothing, of course, and unfortunately you can only turn hidden players on or off when you first create a league- once your league is underway, you're stuck with whatever setting you chose during league creation.