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I just bought a 1989 Four winns 170 Freedom with the 2.3 L omc. Took it out for a quick run and after about 20 mins the motor died while it was at an idle. When i tried restarting it acted as if the battery was dead and would barely crank over. So I tried a different battery, and same thing. According to all the gauges everything was right where it should be.
Could this be a starter issue or something more serious?

On a boat that age it could be a lot of things, if the battery is good, check the battery cables, where they bolt to the starter and engine, if corroded they will cause a slow or no start condition. It could also be the starter, is it original? The one thing peculiar to marine engines that can cause this is a bad exhaust manifold that lets water in the cylinders and hydrolocks the motor (water in the cyl is not compressible like air is and the piston can't move up to the top of its stroke). The way to test this is to remove the spark plugs and crank it over, if water shoots out of the spark plug holes then its hydrolock. You gotta get the water out and change the oil and replace the exhaust manifold.

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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

Ok i removed the 2 spark plugs i could get at wihtout removing some of the exhaust. I did not get any water coming out of the holes but it doesn' crank over more than once or twice everytime you turn the key. Is there a way for the marine shops to test the starter if i remove it? How many cca should my battery have? Any other thoughts?

Yes the starter can be tested by any auto electric shop. They are usually not hard to remove as long as you can get at the bolts. That is a 4 cylinder so a group 24 battery should be adequate. Look at the batt cables if they are original I would replace them the are probably all corroded inside. Go with at least a 2 gauge wire set, 4 gauge is the cheapest thinnest wire but that is probably what the OE is. On my boat the OE wiring was awful, thin cheap garbage. Batt wiring is important esp on a boat, in a wet environment, you want good Ancor Marine cables.
In some cases if the outdrive is low on fluid and locking up the engine won't crank. This is because the outdrive driveshaft and u-joints have to turn whenever the engine is running. If you run the out drive low on oil or if it was changed recently and it wasn't filled right that can happen too.

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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

I agree with Lou. On a boat of that age, I would replace all of the battery cables. Go with the tinned wire, which is what Anchor wire is.