www.iFourWinns.com

Do you have a remote oil filter mount? I’d so check all the lines and the mount itself since those gaskets can leak.
Next get a bright LED flashlight and a mirror to check your oil pan. Sometimes it is as simple as the bolt for the dipstick tube needing to be tightened. But oil pans can rust thru if they were never sprayed with a rust inhibitor. Look for blistering rust on the pan. If you find this you may need to pull the engine and replace the pan.

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88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8

1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II

Also if the pump bearing leaks it’s time for a new one. This is the front circulating pump not the raw water impeller? If so just pick up a Sierra Marine pump they are about $100 and are easy to install. Just like any other Chevy small block.
My engine is on it’s 3rd one.....
Just don’t use an automotive pump it will not last...

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88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8

1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II

Yes fairly common and the front seal for the crank can leak as well

_________________
88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8

1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II

It depends, if it’s only from the timing chain cover probably not but if from the side of the oil pan gasket
You might have to lift the engine.

_________________
88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8

1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II