Some good questions and a lot depends on who you are playing with and who is in the pot with you when you make your moves. If the buy in game is for $5 then forget about bluffing and only play when you hit, people just wont lay down a medium/top pair despite you high raises or reraises.
Try to vary your play up a bit, maybe after you raise preflop, check the flop and reraise any raise, change your play, of course if the other guy checks (depending on his style) you may well be in front and can bet on the turn.
If you raise preflop and the flop shows rags, he may know by your bet that you didnt hit, so will stay in the pot with his low pair.
Also, dont raise the same amount every time, maybe with low pockets, say 55, raise 4 or 5 the BB (depending on table position) and see what happens. Then if you hold AK, maybe make a 3 x BB raise and see if the flop helps
Be selective about your bluffs and dont be afraid to lay down a good hand if the flop doesnt help, its obvious that the flop wont hit every time, and the same will go for your opponents.
Hope this helps and let us know how it goes