Can I play a PlusPower then a Gambler, and play another PlusPower I got from the Gambler?
Yes, you can.
Source: WotC Chat (2000-02-24)

Relevant cards

Note: All applicable cards may not be listed below.
WOTCB1_84
WOTCB2_113
WOTCB2_113
BW1_96
DP1_109
DP3_121
HGSS2_80
PL1_112