This hand gets me into trouble a lot...suggestions?

[IrishPete]

no real hand history to post cus iv noticed this hand more live cash than online, here are the basics.

game is £1-£1 PLHE [so like $2-$2 roughly]. game is very soft, a few decent players but a lot of chasers, calling down with 3rd pair...its a good game.

il have like 88 in middle position and say call a raise [or raise in late position and get reraised and call]
flop comes 679 rainbow. preflop raiser bets, i raise. he shuvs...hmmm. i usually call in that spot [obv as its not too deep, they usually sit with 20-50BB wen i usually sit with 100BB]
doesnt seem to get there as often as i wouldve thought.

General questions:
-is raising there not a great idea, shud i just call and fold the turn if i miss and he fires a pot sized bet?
-if he checks, shud i just check behind or take a shot at the pot? [i would prefer the latter.]
-if the hand is late in the session and im say 200-250BB deep v. guy with same shape of stack, how shud i play the hand?

this hand confuses me a lot, i think maybe i over-estimate the strength of my hand and end up running into an overpair etc.
any help appreciated, realise this post is a bit confusing and all over the place, but as its happened quite a few times, with various preflop situations, its hard to remember exact details! cheers.

IPete.