I have an Abu Orra sx.. First bait caster ive used in over 10 years (last was a Quantum that was stolen from the back of my truck)

Twice now, ive had problems with the line guide sticking on the right side... The first time i fearfully took it apart thinking i would find debri in the worm gear... But there was nothing (that i could see), however i put it back together (somehow) and it worked fine for a couple months

Yesterday i fished a few hours after work, no problems until the last cast... I didn't even notice all the line wrapped around one side of the spool until i threw a big birds nest

I freed the backlash and threw a couple more casts... Wasnt sticking anymore, but it makes me nervous that it could happen at any time

The reel is only 5 months old, and i oil it after every use... Anyone else ever have this problem??

For starters, don't oil it after every use. That does more harm thatngood and is completely unnecessary. Oiling a reel 1-2 a year is plenty. Less is more /w oil on a reel. Excessive oiling can cause internals to slow and impact casting distance. 

As for the line guide sticking, it can be a few things. Being the reel is new, I'd eliminate a worn pawl. Make sure the pawl cap is snug. If it is coming loose, the pawl will shift and come out of place. There could be dirt on the pawl itself. Take it out and clean the tip. Dirt can also be caught in levelwind guide grooves themselves. Take the levelwind gear out and clean it. The sleeve that the levelwind sits in could be sticky on one side as well. make sure there isn't anything keeping the sleeve from moving. I apply a super thin coat to the outside of the sleeve each winter when i tear mine down. Most likely you have dirt or something in the levelwind gear or pawl. If you aren't handy taking a reel apart, you could possibly get lucky and just blow out the gear /w air. Stop oiling the reel so much. 

I should have specified, i only oil the worm gear every trip... Manual said to

Im pretty good at taking things apart, putting them back together is a different story!

Just wondering if this is normal or not?.. I never had this problem with my $40 Quantum, but the $100 Abu does... Go figure??

Chech the pawl cap that it is snug. If so i recommend replacing the worm and pawl as a set. If the cap was left loose for a period the pawl and or worm could have been damaged. 

Pretty sure i got it snug when i put it back together the first time, but seems like i remember it being loose when i took it apart... Not sure on that (drank since then)

Ill look into that, good to know before i buy my next reel too!