bviboater said:
Raise the main while still moored or at anchor. Drink your morning coffee while doing so, that is, take your time there is no rush.

agrimsrud said:
I don't know of any charter boats that have a lazy jack setup as you wish for. If wishes were fishes...
So not much point in telling you that this would help you since that's not the system you're going to have.

Hoisting the main while on the mooring ball is always easiest. But let me suggest two other things to consider.

First a couple of observations. (a) The reason raising the main is tricky is that the sail battens get hooked up on the lazy jack lines. You will continue to fight this problem until the battens are past the lazy jack lines, i.e., once the sail is about 2/3's of the way up you are past the problem. That's a good thing 'cause that's about when things are getting heavy. (b) You have a clear line of sight on both sides of the sail from the mast location. Not so much from the winch location.

We always send a crew to the mast. His/her job is to "sweat" the main halyard, i.e., he/she is not pulling it "up" but rather towards them. The second crew member is at the winch/clutch and pulls the slack out as the person at the mast is sweating the line. The person at the mast has a completely clear view of the sail and can easily determine if the sail is hooked or not. Sometimes the mast person might tell the winch person to lower the sail slightly or tell him to wait a second. But mostly the winch person will pick up the slack as soon as the person working the mast sweats the line. Once the battens clear the lazy jack lines the winch person can send the sail to the top.

In addition to sweating the line at the mast I strongly recommend that you take a look at your auto pilot to see if it has the function to hold the boat at a certain angle to the wind. B&G has this ability and I'm sure Raymarine has the same. I have instructions for the B&G on my web site located here together with a short video. Letting the auto pilot hold the boat 0 degrees to the wind is much much simpler than having the helmsman do this task especially since he may or may not have a clear view of the sail and lazy jacks.
https://www.sv-dreammachine.com/operating-hints

And lastly - it's not a race to get the main up. Better to make sure you're not tangled in the lazy jacks than getting impatient and giving it a good pull. You will pull the lazy jack lines off the mast if you give it a good enough tug.

I also assume that you have the main depowered (e.g. loosened Mainsheet and boom vang?)

NCSailor said:
I don't understand why Moorings doesn't put a screen flap in the Bimini so the captain can see the sail going up. I had this on my 393 and it made life very easy. Not to mention I didn't have to lean out to see the top of the mainsail while underway.