I had a simular problem. When cold it wouldn't easily go into first, then second and third were chores to get it into. I found that if I did the old double clutch trick going into second and third, it would slide right in. Not actually clutching twice, but starting in, the backing off to the neutral position, then back in. I only noticed this with mine when I hadn't driven it for a period of a few days. And if I drove it say 30 miles or so, it would clear up and be fine for what ever time it took until I didn't drive it again for a few days.
My solution was to change out the tranny fluid. A chore in itself as there isn't much room up there for a bottle of mercon to be poured into the fill hole. I also bled the clutch. I didn't see anything come out the clutch, as in bubbles, but better safe than sorry.
Been driving it as normal and the problem has gone away completely. But I'll know more as the seasons change and the temps drop lower than 60 at night.
I've also been driving it more, pulled a 3000 lb horse trailer with a 1000 lb horse, without any ill effects save a little low on horsepower pulling hills.
There can't be more you can do to a tranny except pull it out and rebuild it and change the clutch than what I did. So guess I'd change out the oil, and bleed the clutch first.

 

Someone said they leave the clutch in at lights because you can start again faster when the light turns green. That's really bad for your throwout bearing, so I've been told. I used to do that until a friend of mine enlightened me. If the throwout bearing is indeed the problem, premature ageing can be blamed on this practice. Don't worry about the traffic behind you getting antsy because they don't have to fix it if you break it.

 

on my truck and past ford 5 speeds i have had the "sloppy stick". if you take the shifter out you will notice a 2 pins on either side of the stick at the 'fulcrum' point these pins can where out and hang up. also on older models there is a spring and a washer that keeps pressure pushing down on the stick "making it firm" if..err...when this spring weakens it makes a sloppy stick that can hang up or feel like a bad syncro. the only fix i found was to push the washer down on the spring and hold it place with a hose clamp firmly tightend. it worked for me.. hope it helps

 

try changing the tranny oil first before digging too deep. get some cheap mercon ATF and some high quality ATF like mobile 1 or Royal purple syncromax. drain the old fluid and put the cheap fluid in. then drive it around for a bit. then drain the tranny again and put the high quality stuff in. note the metal shavings on the magnetic drain plug, if there are a lot, the oil is dirty.