1. Sump gasket. I hope you realise you can remove the sump with the engine in place? Not a big job either. But that may not be the source of the leak. A frequent leak, that ends up there, is the rocker cover gasket or the oil feed to the head at the back.
2. Clutch. Top two gears have synchromesh, which explains why less problems with these. If you can engage first or reverse when stopped without noise, there is nothing wrong with the clutch and the issue is your driving expertise. If it clashes engaging these when stopped and pausing a few seconds before engaging, the issue is almost certainly the clutch mechanism, not the clutch itself. It will be either the hydraulics, or one of the two cross pins that connect the tube between clutch release shaft and the slave cylinder bell crank, just outside the bell housing. If it is an early style slave cylinder setup, the pushrod is adjustable.
Hope this helps 
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				John
JDNSW
1986 110 County 3.9 diesel
1970 2a 109 2.25 petrol
			
			
		 
	
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