Be especially mindful of overhead power lines. Even experienced trailer sailors have had fatal accidents when rigging on land.
Looking at the photo, I'd want to see the boat secured better before the mast was stepped and any sails were rigged. Not just supported better, but strapped down. Also, choose a very calm day and don't cleat off the mainsheet.
I actually like the idea of rigging indoors in your shop (again, watching for electric lines). If the wind pipes up quickly where you live, this is probably the best bet.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT