Tested a Winchester 290 I was given and noticed a couple things. When you go to charge a round the firing block will get stuck halfway and if pressure is applied it will go forward and the hammer will fall. (Without touching the trigger) Also tested with safety on still happens and hammer falls. Also this happens almost everytime. Any ideas?

I have a rebranded Winchester 190 sold by Sears & Roebuck, basically the 290 was nicer version with checkered stock and better blueing.   The trigger housing (Fire Conrol Group) FCG is held in place by a plastic roll pin.  Push the pin out and the trigger FCG comes out the bottom.  The FCG housing could be filthy impeding function.  I'd probably give it a good dose of Kroil or other penetrating oil and give it a good cleaning.

The bolt can be removed once the FCG has been removed.   The charging handle is removeable by just pulling it out once the bolt is lined up with a takedown recess (about 1/2 way retracted IIRC).   This frees the bolt to where it can be retracted and removed through the bottom.  There is a plastic guide rod with spring in the rear of the bolt.  I'd remove the bolt and give it a good cleaning.  If I remember correctly there is a cocking arm from the fire control group that rides in a notch on the side of the bolt.  When reassembling the bolt the cocking bar has to slip back into the notch of the bolt.  Sounds like the cocking arm maybe sticking, you might be able to see worn parts or a broken spring.

The most difficult part is gettting the recoil spring and guide compressed while trying to get the bolt reinserted into the receiver.  I use a small screw driver to stack  the recoil spring/guide rod back into the bolt and try to hold the spring while reinserting the bolt.  The recoil spring has a lot of pressure and the plastic guide rod can fly like a missle!   Ask me how I know.    

The only real problem I had with my Sears was light firing pin strkes.  I found the problem was the barrel nut worked loose allow the barrel to move forward away from the closed bolt.  When the barrel nut came loose the front hand guard also got loose.  I tightned the nut a couple of times but it always worked loose.  The last time it came loose I put Loctite on the barrel nut and has not come loose since using Loctite.

Numerich arms have a very good schematic of the Winchester 190/290 and have many of the parts in stock.

I went ahead and tightened the barrel nut. (It was only on with 2 threads..woops) I also went ahead and just now took the FCG and the bolt out again to clean it some more. It was pretty dirty the first cleaning and maybe I missed something. I'll report back when finished and let you know how it goes.

I just got don'e reassembling and noticed it still gets stuck half ay (Looks to be getting stuck on that cocking arm). And if you let it go fast it still fires.

I hope you figure it out, I would be hesitent taking the fire control group apart, I did that to an old Marlin semi auto and it took two of us a long time to get everything to line back up.  In the factory they use special jigs and tools to assemble.  If you had a parts degreasing bath like they have in machine or auto motive shop I would try and clean the FCG.  Kroil and high pressure air will go a long way to in cleaing the FCG.  Maybe you'll be able to see a worn or broken part.  If someone dropped the FCG on the cocking bar it could get bent or out of allignment.