Re: Chapter 1: Our first cruise
A rolling hitch as cited previously is the main way to get the tension off, but then you still need (and should always have) a 'marlin spike' on your knife/person - basically it's just a knot picker. Your basic knife (you do always have a knife available?) from WM has a blade and marlin spike for 19 bucks.
The other thing I'd recommend is to use McLube or some other dry lube on your main slugs and slot. Your avatar shows you to be relatively young, you should be able to hoist a Watkins 27's main hand over hand (no winch) to the top and then just use the winch to set tension. That (lube) will also make is set better.
That's provided you are headed into the wind, any deviance from dead in can put premature pressure on the sail and make hoisting difficult and even impossible.
I don't know your commuting situation, but you may find it helpful to go out and single hand, starting with just the main, then adding the jib. Get comfy on the boat by yourself - then add the wife and daughter. A confident skipper who knows the boat goes a long way to making crew feel good and times enjoyable. Find a friend to help if you need to.
Good luck, have fun and stay safe.
Lessons learned are opportunities earned.