Table is very loose passive (6+ to the flop 90% of the time) where raises are generally NOT respected; this is especially true preflop (some players will cold call a raise with any two suited).

1) Is it still a good idea to raise 99+ from the blinds?

According to SSH it is, but what is the reasoning behind this? Yes, I understand that you are likely ahead PF and that you should push this edge, but more often than not when the flop comes down you will be behind. Say you hold TT and raise from BB, 5 limpers + SB call. Flop comes all rags, you hold TP. When you bet out, you still are giving good pot odds for overcards, straight draws and flush draws. Even going for a c/r these players will still call you down, as your c/r builds the pot for them to correctly call (which is insignificant since most of these players will chase a backdoor flush draw with no pot odds whatsoever). The only time you will truely have a strong hand is when you hit your T on the flop. And even then you are vulnerable to flushes and straights, at least you still have draws to the boat or quads.

2) Raising PF with hands like AKs, AKo, AQs, etc. When you miss the flop,

e.g. J[img]/images/graemlins/heart.gif[/img] 2[img]/images/graemlins/heart.gif[/img] 6[img]/images/graemlins/spade.gif[/img] (7 players),
checks to you at CO with A[img]/images/graemlins/diamond.gif[/img] K[img]/images/graemlins/diamond.gif[/img]

should you still make a CB and draw to your 4 outer overcard draw and backdoor SD knowing full well at least 3 others players will call? (someone will likely have a flush draw, while the others could hold a Jx, or a gutshot/OESD) Or is it better to check behind and fold to a turn bet UI.