Ill add to this later. I would get a hold of Fingersandteeth(Deri) since he is the king of maps.
Here is a map guide from Holocron
http://www.the-holocron.com/index.php?option=com_content&task=view&id=98&Itemid=46

Well I pick my squad first
Then if its melee or shooter I go from there and any other benefits the squad has(swap override Superstealth)

This is more of a list than questions but i hope it helps.
Melee maps
Ruined Base,Cloud City,Train(great for double override),C.Starship,old Munn,and rancor in away.

Swap Maps
Starship,Rancor,C.Starship and Ruined Base sometimes. Jedi Temple is a great map for a Yodabuck swap squad.

Shooter maps
Death Star
Taris
Starship
Jedi Temple
Teth for Luke SS
Hoth outpost


Swap or deep strikes
pawn strafe(starship),Speeder maps(teth and Taris easy for the speeder to move in and out can go about anywhere on those to maps. B&B likes Rancor or Starship since its easy to go 18 squares.

Can I get to Gambit first round? Some maps let you get first round gambit without movement others dont. On most maps there is one side that can get first round Gambit

Double override?
maps Cloud City,Train,Ruined Base,C.Starship.

I have Cloak or SS whats a good map?
(mos Eisley for Nom bombs)
Death Star
Hoth for mando scouts
Rancor


What side of the map is better for my squad?
Some squads play better from one side.
side note
If I win map should I defer side so I can strike to their placement.

Do I know the map good enough to play it in a big tournament?
or will not knowing the map that well give me more trouble than its worth. This came into affect at Gencon For me.

I would ask the following:

For competitive (tournament) play, there are some map features that help to define a good, playable map: protected starting areas to prevent first-round attacks, a measure of cover in and around gambit to give melee some protection, and multiple options for movement towards gambit that allow squads to advance without getting picked off. Beyond those three, what other features do you value most in a competitive skirmish map?