Okay. I am pretty confident that this is a synchro issue.
Here is a video that illustrates this better than I can explain it. Link at the bottom of this post. Feel free to fast forward to the 3:30 minute mark as this is where they talk about the synchro ring.
Basically, this ring begins to wear out and as you press the shifter into first gear the ring does not do as good of a job of lining those gear teeth up and requires you to put more and more pressure on it in order to get it in. While you are moving the vehicle it relieves the pressure a little on this ring which is why it is easy to get in while you are in motion. First and second share the sleeve that goes over the ring and are the two gears that get the most use which is why they are harder. The gears and synchro rings and sleeves on the other gears, including reverse are not as worn which is why they are not affected.
I would suggest to deal with it as long as you can and then have the transmission rebuilt. You are not going to do any more damage to them but they will get harder and harder until they don't go into gear anymore. So clearly don't wait to long but the idea would be that when they go into the transmission to fix this, they would put a new clutch assembly in as well because there is no additional labor. With this being the idea, you want to get as much use out of this clutch as possible.
However, if you decide to just have it done now, they can inspect the clutch and replace as needed. Hopefully this helps.
https://youtu.be/wCu9W9xNwtI
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Thursday, April 18th, 2019 AT 2:40 PM