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When the starter is out of the engine its in the same position. when i power it, the gear extends out and it spins. But when the starter is installed the gear at rest is already meshed with the flywheel. Could the issue be with the flywheel? (which i really hope it isn't)

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This may be the problem. When you install the starter (with the pinion gear retracted) you should have a gap between the pinion and ring gear of about 1/8". If not, you need to determine if the problem is with the starter or the flywheel.

Remove the starter and use some calipers or a ruler to determine the distance from the starter mounting surface to the nearest face of the ring gear. The distance should be 1-1/16" give or take 1/16".

Then measure the "stick-out" of the pinion gear on the starter with the pinion gear retracted. Measure from the mounting surface on the starter to the end of the pinion gear. This dimension should be 15/16" give or take.

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