I would suspect the Clutch Slave Cylinder being at fault or not moving far enough to operate the clutch.

Videos to install bushings
http://www.marlincrawler.com/transmi...ver-ball-seats at the top right part of the screen.

http://www.marlincrawler.com/tech/gu...t-installation

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Well I just changed the clutch slave cylinder ($13 )
and it's still hard to put in first gear
I flushed out the clutch fluid and bled that and my brakes since I put new brake hoses. I took it for a nice long drive around my neighborhood and further without any problems.
Shifting was great along with the brakes.
The only shifting problem is putting it in first when I'm at a stop and putting it in reverse. That bish grinds going into reverse but you guys did say it has no syncro.
I really hope that flushing out the Trans fluid with the red line fluid takes care of the problem.

 

I see something that looks large bolt that had two wires coming out that are cut .... anyone know what it is?
I also noticed a rear shafts seal leak on my Trans where the drive shaft connects. I should replace that before I put in the red line mt90 huh

 

Well I broke the smaller 17mm bolt on the side of the trans loose and gear oil came pouring out! I guess it's been serviced in the past but the oil was black and way overfilled.
I jacked up the rear diff and some more oil came out. It's been draining from the drainbolt for a few hours now.

 

I was going to use a pump to pump in the fluid through the fill/check hole but I decided to do it through the shifter so I can see the condition of the shifter seat bushing. Two birds with one stone thing.....
It would have helped if I knew how thick the seat bushing is supposed to be but it was very easy to fill the trans that way
It's much easier to put the trans in first now and the only other problem was 4th while driving but that's also smooth shifting now
This job was cake compared to flushing the trans on my 2008 Toyota sequoia (5.7L)

 

I had the exact same problem as OP and a good old fashion clutch bleed did the trick! Despite the fluid in the reservoir looking good, it came out all brown through the bleeder. Some air too.

 

TL;DR - Had similar issues, got the short shift kit from LCE and all was good-ish.

I have an 87 too. You prob have the W56-B transmission which can bee seen on the firewall plate or by looking at the shifter. Ours should have 6 bolts holding the shifter base plate to the trans. I was having similar problems getting mine into first when I first got it. Bleeding didnt help and had no clutch bracket fatigue D&F with GL-4 with no luck. The shifter was loose so I planned to get the LCE red seat and nylon cup. Ended up getting the short shift kit from them because it was $100 and came with the seat/cup. Since install I've had no issues getting it into gear and it shifts smooth. However, got it knowing it had transmission issues as I do have a noisy input shaft bearing and a 4th gear syncro going out. Just picked up a used W56-B and am replacing the input shaft bearing and resealing it with new gaskets and seals. Replacing the rear main seal, clutch and putting redline MT90 when I get around to the swap soon too.

 

I'd love to buy a new short shifter for $100

 

http://www.lceperformance.com/Short-...-p/1097004.htm