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Re: why it is difficult to engage the gear when the gear...
This may be wear clutch related, if the clutch is starting to wear out past a certain point of clutch disk thickness the trans gears don't stop when you press the clutch in, this causes hard to shift issues like yours, one question does the clutch feel soft ot have to much play?
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If this is a Ford vehicle it likely is a stripped gear in the blend door motor, which looks like a 4x4" box 1" thick held to the heater plastic box with three or four screws. This part can be ordered online for about $30 and is not difficult to replace on most vehicles.
The wires have a connector that is fairly easy to pinch and pull to release. The little motor box can be unsnapped and opened to view to see if the gear is not engaging or is missing a tooth before ordering the replacement. There will be grease on the gear so have a rag handy to wipe it to be able to inspect for damage. The identical cog gears are extremely difficult to find so don't waste your time trying to replace the little cog that strips out in these.
A high clutch pedal is good.
There should only be about a half inch of pedal freeplay, before you start to feel resistance.
So the clutch should not engage until it is almost fully released, near the top.
The makes shifting the easiest.
If the shifting is difficult when cold, then put the transmission in neutral and let the clutch out when you warm up the engine.
That will warm up the transmission oil.
Of course you could also check the transmission oil level and change it.
But your question makes me believe you may need more experience on a stick shift. Make sure you do the H pattern carefully, and do not get lazy and turn it into an X pattern.