14-3.... You only need 2 conductors black/hot white/neutral (plus a ground).
15a breaker...OK
GFCI.... I would install one for any outdoor wiring.
Wire in conduit.....NO You cannot run any cable NM or UF in a conduit. Use TW or THW stranded wire. For a 100ft run w/800 watts it wouldn't hurt to go up one size to #12
2 hots from switch?.....Only the black/hot gets switched, the white/neutral does not. The switched hot,neutral, and ground go to the first light. From there they continue to the 2nd and then 3rd and so on to the last one.
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