Toyanvil is not crazy; he responded to a post that I subsequently deleted so I could change some wording and hopefully prevent some irrelevant nitpicking.
The "improved" post follows:
Randall,
A partial list of things that
could cause the problem you described includes:
1. Mis-adjusted or incorrectly installed clutch master cylinder linkage
2. Incorrect clutch master cylinder
3. Internally leaking clutch master cylinder
3. Excessive expansion of the flexible clutch hydraulic hose
4. Incorrect clutch slave cylinder
5. Incorrectly mounted clutch slave cylinder
6. Internally leaking clutch slave cylinder
7. Incorrect, damaged or worn clutch throw-out lever or pivot ball
8. Damaged or excessively worn throw-out bearing
9. Damaged or excessively worn clutch cover
10.Partially delaminated clutch disk
11. Incorrect clutch release system hydraulic fluid
12. Incorrect transmission lubricant
Having to "pump up" a hydraulic clutch linkage system before being able to engage a gear suggests that either the clutch is not being completely disengaged or that the clutch is not remaining completely disengaged long enough to make the shift.
The first step is to determine (a) whether or not the clutch is properly disengaging and (b) whether or not the clutch is remaining completely disengaged. With the engine NOT running (and the parking brake dis-engaged), put the transmission in first gear and fully depress / hold the clutch pedal. If you can initially easily roll the car forward / backward, then the clutch is completely disengaged and most of the possible causes can be eliminated. Continue to hold the clutch pedal fully depressed for 10-15 seconds; if you can still easily roll the car forward / backward, internal leakage in the master and slave cylinders can be eliminated.
If the clutch is not completely and persistently releasing, you need to determine why not and correct the cause(s). If the clutch release system is working correctly, then you probably need to look at the transmission.
Never say never, but the problem you described does not strike me as being a transmission issue.