www.iFourWinns.com

I have a relatively slow leak behind the engine. Any ideas of what this could be?
I thought about removing the out drive this fall to see if it was a seal.
I am getting tired of flipping on the bilge pump every 20 minutes or so.

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1995 Four Winns 190 Horizon
5.0 Liter Cobra SX drive

I would be pulling off the outdrive now actually, because if your driveshaft bellows is leaking, then it is going to cause other damage such as rusting your gimble bearing, u joints and driveshaft. Unless the drive was pulled recently and you know the d/s bellows is good. That's about the easiest leak to fix, other transom related leaks are more complex. Possible causes:
transom seal (requires drive removal, engine removal and taking apart the transom mount)
transom rotting (all of the above plus transom repair)
Y pipe leaking either at the seal or its corroded (same as above)

While a leaking bellows ain't great its way better than the other possibilities.

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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

Given the age of your boat & the rate of your leak it should be looked at sooner than later.

+1

That's a great summary.

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"Knot Easy" 2000 Horizon 240 Volvo 5.7GS /SX
tow: 2017 Honda PILOT EXL-AWD
prev. boats:
'87 Chaparral 198CXL 4.3 OMC Cobra
'69 Jetstar 16ft Ski Boat, 115hp Yamaha
'68 Aluminum Jon Boat, 3hp Sears
'64 Water Wings