This is a long winded post, but wanted to give as much info as possible....

Let me start by saying I rode dirt bikes as a kid and have not riden in 20 years, bought my first big bike in April 2011 (2007 Softail Heritage Classic - 18000 miles). I have put 1200 miles on since April and am starting to feel comfortable on it and absolutly love riding it. Unfortunately, my lack of riding experience leaves me wondering what is normal and what I need to be concerned about. I have a manual and some mechanical abilities and enjoy doing some work on my own, but I also paid for extended warranty and would prefer to allow the pros to do advanced work and work involving special tools.

I feel a slight wobble that happens at various speeds. At slow speeds there are times when it rides great and others when it seems almost impossible to keep it straight (when rolling to a stop is when I notice it most but it is intermittent). At all speeds I can feel periodic slight side to side waggle that does not seem normal. If I take my hands off the bars it will immediately vear left 100% of the time. When making a right hand turn around curves I can hear a squeak that sounds like it is coming from the front wheel. When riding at any speed it sometimes feels like a pulsing drag like I am hitting gusts of head on wind. The front wheel is down to about 3/16 tread. The wear looks normal- no obvious cupping, but I am not sure I would recognize slight cupping.

I have read a lot of threads on wobble, but none seem to fit my symptoms exctly. Here is what I have done so far..

-Put it on jack and checked for play in front wheel.. can't feel any.
-spun wheel -could not detect out of round/side to side movement
-spun wheel - does not seem like excessive drag from brakes or grinding/noise from bearings, but my experience on this is limited.
-Did fall away test and it seemed a little loose - tightened it up a bit following manual and forum post instructions - no change to issues.
-Took it to dealer and asked them to check it out - paid $50 warranty co-pay and they said everything is fine and they regreased the steering tree. They said spokes are fine, wheel is fine, tire is fine but should be replaced soon and they feel it rides fine.

My problem is I don't have enough experience to say if this is normal or if there is a problem. My feeling is the squeak and wobble seem like a wheel bearing going out and there are a number of forum posts that seem to make this a legitimate concern. I am nervous about the bearing going out completely while cruising a curving mountain road. It seemed like the dealer was more interested in getting me out of their shop than really looking for an issue. I am thinking of replacing the front tire since it is toward end of life so that would be a good time to have bearings checked/replaced.

What do you guys/gals think? Am I just overthinking this and feeling something that isn't really there? Since the dealer doesn't see a problem, do I take it in and tell them to replace the bearings for piece of mind and pay it myself rather than getting the warranty to pay? Is it something else completely?

Again, I am sorry for long-winded post. I admit I have limited knowledge/experience and would greatly appreciate any advice I can get from the more experienced riders on this forum.