Bungee cord to "tame the tiller."
Head into the wind as best you can with a slight forward movement...
Ease the mainsheet completely (it'll flop some as you raise).
The sail slugs and the halyard run to the cockpit is really only useful together... if you are going to remain bolt rope the halyard to the cockpit will actually be a pain.
I am a 25 foot sailboat with bolt rope main, with the halyard run to the cockpit, and I usually jump the rope before the deck organizer when I am solo, and raise the main myself that way, then I take up the slack to the halyard after it's up.
But yeah, I'm on a tight lake in the hills too, and the gusts are brutal. Here's the best suggestion I can give you... duck deep into a cove on a windward side (to get shelter), head into the wind, you should have a drop of 50% or better of wind speed, THIS should get you a decent quiet place to raise your mainsail (this is how I do it solo sailing when the winds pipe up, but I still want to sail).
By the way that 165 is a sweet little wing keel boat, you'll have some fun with that. That was on my list at one point in my ladder of upgrade boats.
Welcome to the obsession.
PS. I get that the boat is a might bit tender for going forward to raise the main. You'll likely be MUCH happier with sail slugs, and a sail stopper, and that halyard run to the cockpit as you mocked up (I know - winter project - I am familiar with that)... this was my last winter: www.shnool.com - /images/capri25/Boat Projects-2012/
You'll get use to it all though.