Yes been there. What I found is I installed The new wiring harness up grade years ago. When I did it he wanted them all spliced. So if I remember as our boat is 1200 miles away as we bought his boat many years back.  It was the purple wire in the engine compartment.  I developed a leak in our antifreeze over flow tank. This got into the connection and coroaded the connection. It created that same issue.  So all I can say is trace all of your start circuit wires and connections. This happened when we were pulling into Norfolk with navy ships in motion. Not fun. 

Bob,
Have you read this?
https://www.catalina36.org/members/important-notices/corrosion-and-your-...
 

I also have had the same issue on my '83. In the last 2 years I have replaced the starter (when it failed), but the problem of having to push the starter button multiple times resurfaced. I then replaced the key switch and the starter button switch as well. It still happened last weekend.
I'm going to trace the wiring to see if I can find a questionable connection - I'll try to post my findings.
Bob, I see you are also on the Great Lakes. Salt is not likely to be our issue, but I suppose the age of the wiring could be a culprit. The wiring on my boat has always been a little suspect due to many changes made over the years by the PO.
I hate when you push that stupid button and nothing happens.

Hi,

I have a 1988 Mark 1 that does not start. It worked earlier today flawlessly. Then I went out 6 hours later, turned on the power (it had been turned off so the batteries would not get drained) and everything lights up when I turn the key, but the silver button does nothing at all - not even a click. Bad connection? Or something else? The boat was pitching a bit on the mooring so I suspect the loose connection, but there was nothing obvious when I checked the wiring.

Thanks,
Aaron

This turned out to be a bad starter button. I ended up replacing the button.

I recently had that same problem as well. I set the house battery switch to "all" and it worked. The starter battery lug was loose. Later it had the same problem - it was the starter button. I replaced it - no more problem. To keep the battery terminals clean I coat the lugs with lanolin.

I have a 1984 Catalina 36 Hull # 260 and just for the first time experienced the same problem.  My starter switch is a " pull " type not a " push."  This is never a good thing and has me concerned.  It did start the second time I pulled the switch out.  I have Three (3) Size 31 Batteries, so I can put plenty of Amps to the starter.  However, if it is a switch or wiring problem that would be more difficult to find.

I had a problem with the starter a few years ago. After I was sailing with the motor off for a few hours the starter would not engage. I had this same problem when I had my first car, a 1948 Ford, V-8. What I was told by an old auto mechanic at that time was the bendix was sticking. Tap the starter motor with a wrench or other solid object and it would start as soon as I got back into my car and hit the starter. So when my sailboat motor would not engage I simply did the same thing, hit the starter with a wrench then it started for a few times without a problem. I eventually put in a new starter because our bendix is incorporated in the starter housing and it still works fine.

The issues for this have been documented many times.  If you haven't replaced the trailer wiring harness connectors, it is time to do so.

I am sure it's here on your website, here's one of ours:

http://c34.org/bbs/index.php/topic,5078.msg35943.html#msg35943

Alo in that thread is a discussion of Starter Problems, the fuseholder on the wire from the start button to the starter solenoid.

Bob
It has also been my experience that if you push the starter button and the volt meter goes all the way over, but the starter does not engage then the problem is in the starter. If the volt meter does not move when the starter button is pushed then it is probably an electrical problem with the button, fuse or lose wire. But, you probably already know this.

Went through this myself this Spring. There's a lot of threads and good info on this on the site. The solutions for me were multiple

1. Loose connections. Several had vibrated loose over years
2. Corroded connections. A combination of oil and anti-freeze spills had compromised connections in the engine compartment. Salt and age had corroded a connection in the instrument panel
3. Old wires. One of the wires was so brittle that it snapped in my hand as I checked the connection

This took about 4-5 hours to troubleshoot. It was a really valuable exercise because I now know what/where every wire does/goes between the battery, the engine and the panel. Future troubleshooting time will be greatly reduced. Secondly, the engine starts reliably now. Finally, I discovered new items that require attention in the wiring. I will tackle these over the coming months as none of them are critical.

Hope this is helpful

Had a similar "intermittent start" issue several years ago... after checking several things, found a poor crimp connection on a wire at the starter motor (wire broke at crimp when I wiggled it...)