I drove the car earlier today and noticed the oil under the car. I always thought it as the crush washer from the oil plan not being replaced, but I noticed gear oil pooling where the bell housing and dust over meets.

I have noticed once the car is warm, it is difficult to shift into first gear at times, and it has grinded in 3 occasions.

any ideas what I would need to replace, and if this is the reason for the difficulty getting into first?

 

 

 

If you have ruled out a leaking clutch master and slave cylinder as the culprit, then I would look manual transmission oil seal.

If it’s gear oil that’s not hard to determine. Have you noticed a major oil leak under the trans. Could be multiple problems starting with the clutch master and slave. Try bleeding the system first and check the trans level for oil.

Could be the front seal or the front cover gasket.  Both require removal to fix.

Use a piece of wire or a long skinny stick in the fill hole to see how low the level is.  

 

I took a look under the car. I see oil seeping through the oil pan gasket, and gear oil seeping through the bell housing where the transmission mates with the engine.

at this pint I’m pretty sure seals and gaskets need to be replaced.

A bad crankshaft rear main seal will look just like that.  What does the oil smell like?  Gear oil has a very strong odor while engine oil has very little smell.  Is your clutch slave wet as well?  It's very common for the clutch slave to fail which causes the hard engagements.  

No matter what, the trans has to come out.  I did mine a few weeks ago for similar leaks.  My rear main seal as well as the trans output shaft seal and speedometer O ring were all leaking badly.  The job isn't too bad, but there are quite a few things that have to come apart.  The exhaust, driveshaft, starter, clutch slave, console, shifter, and speedo cable must come off before you can pull the trans.  While you are in there, replace the rear main seal, clutch kit if it hasn't been done in a while, and slave.  Pulling the trans is not hard, but you don't want to pull it again in 6 months to replace something you didn't do this time.

Read my "what did you do today 2023" post about making alignment pins.  They turn a frustrating job into a piece of cake when you reinstall the trans.

The oil has a slight gear oil smell, but not as pungent (I figure due to small amount in finger).

the clutch slave isn’t wet at all, nor do I see any leakage. As for the oil pan, do I understand that’s gear oil?

 

 

I do see it’s wet in these two areas, where dust cover connects into the engine black.

 

Additionally, may sound dumb, but the oil pan wetness I understand is motor oil. If it’s gear oil, could you explain how it could be?

I am still learning.

Go buy some gunk degreaser and clean the bottom area. Either way the transmission needs to come out to do any of the repairs needed. Common problem. Better to drop it and everything will become obvious 

The pan holds engine oil and that's a common leak point as is the rear main seal.  When the RMS (Rear Main Seal) leaks, the oil will come out all around the dust shield and drip out of the weep hole of the bellhousing.  If you really want to know, you can get the car in the air on jack stands and pull the rubber boot around the clutch release fork.  With a borescope ($20 from Amazon), you can look towards the rear and see if there is a gear oil stream coming from the trans input shaft seal area.  Again, other than ordering parts ahead of time, it desn't really matter.  The trans has to come out either way.  The seals are cheap, so just replace the RMS no matter what.  The oil pan gasket can be done with the engine in and on the mounts, but it's tight.  

Are you going to do the work yourself?  

Debating. The car is jacked at the front with a 45° angle. At this angle for the past few hours, there has been no leaking.

It’s safe to say it’s parked for good now. I’ve been quoted by Godzilla Raceworks for the repair at about $950 with labor. Really don’t want to pay that kind of money, but really don’t want to pull the transmission out either. Gonna see what the options are if I do it myself.

I was going to get the carbs tuned this week before garaging for winter then this was discovered. 

 

Did you check the transmission fluid level yet? Check it with car level.

Leaks aren't the end of the world. As long as it has enough fluid in it. Heck, on some cars leaks are how you know it has oil in it!! 🤣