What's your strike telling you?
A lot can be learned just from taking a close look at the strike. After some time, a latch strike will show some signs of wear. If that wear is at or below the opening in the strike, your door may be sagging, keeping the latch from entering the strike reliably. Same with the strike for your bolt, though in that case, the wear will be on the bottom edge of the opening in the strike or it may show on the bottom of the bolt itself. When this type of wear can be seen, the repair might be as simple as tightening the hinge screws, which will pull the opposite side of the door (where the locks are mounted) up.
Similarly, look for marks on the wood behind the strike. The wood will often become darkened where rubbed by the strike or bolt. In the photo above, more wood needs to be cleared out from behind the opening in the strike. This type of wear makes the lock more difficult to operate and often leads to premature failure of the latch or strike.
Locks should operate easily. You shouldn't need to push, pull, or lift the door to get the lock to work; and locks simply aren't built to withstand this type of binding pressure, leading to failures.
The photo above shows what appears to be a latch strike, but was actually used with a deadbolt. The dark marks on the wood at the very back of the opening are a pretty sure sign that the opening isn't deep enough for the deadbolt to extend completely. As seen on one of the videos on our website, a deadbolt doesn't really "lock" until the bolt is fully extended.
You should also remember that, regardless of the quality of your lock, your door is only as secure as the strike it engages in the frame. Reinforced strikes like those made by Door Devil are an excellent upgrade. But, at the least, use screws long enough to tie the strike into the wall framing around the door - typically 2-1/2 to 3 inches long - much longer than screws normally provided by the lock manufacturers.