I will not be in the water for a couple of more weeks but I had this happen a few times last year and seems to be getting worse (more frequent) from what I remember. I have a '91 Chaparral 20' with a 5.7 DP. I have owned the boat since 2000 and it is in generally very good shape despite having over 1,000 hours.

Here is the problem. It starts and runs fine but I noticed the problem when trying to teach my son to ski. Once the engine is warm and you have used it it a while it is reluctant to come out of neutral and into gear (particlularly when doing it over and over again - such as teaching someone to ski). I either have to put it in gear very gently and idle for a few seconds (not easy with a beginning skier trying to hang on) and then accelerate or I can try to accelerate as is normal with a skier. When the second option is chosen (it is preferred) it may or may not 'catch'. It will either spin as if in neutral and then SLAM into gear or I (once noticing this) I will throttle back and try again.

As I said it is only really an issue when trying to teach new skiers and there is no such problem when cold. There is never a problem once you are moving. Sorry for the long post.

Suggestions? Thanks very much in advance.

I would say your shift cables are out of adjustment.

Would this make it react differently when cold vs when hot?

Anything is possible.

If the clutch is not engaging fully, when it is cold the fluid is thicker which may help to suck it into gear. Once warmed up, the fluid may not be able to exert enough force to pull it the rest of the way into gear.

I would check the shift cable adjustment and also check the fluid levels on the drive for good measure.
Hope this helps
Ardy
South Oz

I think Silverbullet is onto something. Sounds like a cable problem.

At that age you may be due for new cables if they have never been replaced. Also a good time to replace the bellows if those have never been changed.