Size one case and drop it into the barrel. It should drop in easily and fall out when the barrel is tipped up. Now try another test. Take an empty case and see if one of your bullets will slide into the case with a little pressure. When the bullet just drops in you will need to size just enough to allow some resistance to keep the bullet from falling into to the case and not too much so you can push the bullet in with finger pressure. Now what you do with this is place a bullet in the case and make certain it is much longer than you would normally load it at. Place the bullet in the chamber of your barrel and slowly press on the case until it bottoms out. When you remove the case you should have a bullet length that is at the rifling. You might need to place your finger and thumb over the bullet and case to keep it from setting deeper in the case while you are measuring it. Reduce .005 to .010" less and this should give you a max OAL you can use as far as the chamber is concerned. You will have to still make a dummy round fully crimped to try in magazine and loaded to the bottom of it to find out if it is also a good OAL for the magazine.
Having the OAL right should help a lot in your rounds going into the chamber when you use them. Any or all of these uses of your bullets and cases can easily be pulled with a bullet puller to be reused for ammo to shoot.
You can also measure the diameter of the bullet you are loading and then measuring the case with a loaded bullet near the end of the case. It should measure the width of the bullet plus two times the thickness of the case and could even be .001 to .002" less. This tells you the crimp is not too much and is just right.
Finished ammo should drop into the barrel with just the weight of the bullet and fully seat. Tipping the barrel up the round should drop out and hopefully fall into your waiting hand.