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I figured that I would wait until the turn to raise for several reasons. These may be wrong and I hope someone will tell me if they are.
No one is folding after committing one bet on the flop. If they have a flush draw, or str8 flush draw, or just a str8 draw, they would call the raise, have a good idea that I had trips & check it to me on the turn and re-draw for the river.
If the turn card looks pretty safe I feel confident that I have the best hand and can trap everyone for 2 big bets on the turn given I have great position. The turn 3-bet from the bb was unexpected.
In the end, a blank hit the river, the bb bet, UTG1 called, MP2 folded and I called. bb showed J5, UTG1 showed AK, and I lost the pot w/ trip 5's and 4 kicker.
Final Pot: 18 BB

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A raise is forcing BB to call 2 cold, getting 3.25:1, which is technically not enough for a straight or flush draw, and he just might fold on this board. Furthermore, if he does "call anyway" then he is making a -EV move, while you are making a +EV move. Bet it now. Furthermore, BB UTG+1 has not defined his hand. He may be betting out with overcards or a mid-PP because he feels he has the best hand. Even if he 3-bets, you will both be trapping MP2 in between. Again, -EV for him.