1996 Ranger Difficult Shifting

[Shotrod69]

I’ve got a 1996 2.3 with the 5 speed.
It’s having some difficulty shifting.
I am trying to find out if it is a shifter bushing or clutch related problem. I would like to know some other diag things I can do that’s minimally invasive if that make sense.
Symptoms:
Shifting is very notchy, I’ve read that these are notchy trans but my 93 wasn’t this bad.
It just started grinding when trying to go into reverse, it is difficult to replicate. It just does it sometimes.
When trans grinds reverse it won’t go into any other gear. I have to shut the truck off, put it in gear then start it. After that it shifts fine.
Related to above symptom; Even if I don’t start it in gear the problem go away.
I also just noticed that there’s a faint squeal when pushing it into another gear. It sounds like someone else’s car up the road has a squeaky serpentine belt.

Maintenance done on trans:
Changed fluid hoping that’d fix the shifting issue. No change.

 

[4x4junkie]

This sounds like it could be a clutch issue or fluid issue... (at least all except the part about it squealing... that part sounds like possibly the TO bearing going out)
Bad shifter bushings generally present as an excessively-floppy stick handle.

The way I've been able to distinguish a clutch issue from a fluid issue is as follows:
With the engine running, push the clutch in while holding light pressure on the stick as if you're trying to shift it into 1st gear...

If the shifter drops easily into gear after about 5-7 seconds of lightly putting pressure on it, it's a fluid issue (someone possibly put Mercon V or an incompatible fluid in it at some point).
If the shifter continues to be stubborn and won't go into gear easily at all, it's a clutch issue.

 

[scotts90ranger]

The not being able to shift until the engine is off sounds like air in the master cylinder to me but I agree with junkie above me...

 

[Shotrod69]

This sounds like it could be a clutch issue or fluid issue... (at least all except the part about it squealing... that part sounds like possibly the TO bearing going out)
Bad shifter bushings generally present as an excessively-floppy stick handle.

The way I've been able to distinguish a clutch issue from a fluid issue is as follows:
With the engine running, push the clutch in while holding light pressure on the stick as if you're trying to shift it into 1st gear...

If the shifter drops easily into gear after about 5-7 seconds of lightly putting pressure on it, it's a fluid issue (someone possibly put Mercon V or an incompatible fluid in it at some point).
If the shifter continues to be stubborn and won't go into gear easily at all, it's a clutch issue.

The squealing is inconsistent and only happens if pressure is put on the shifter.
When you say fluid do you mean trans fluid or clutch fluid? The trans fluid was drained and replaced with ATF.
The truck also has at least 254k on it, the odometer stopped working.