Congratulations on the boler & the baby! I’m a recent 1st time grandmother myself, only downfall is it does make one want to stick closer to home.
I would get the trailer jack (your wheeled tongue thing), it’s easy to install & can’t imagine camping without it. I installed mine, I’m 67 & not mechanical at all. When I read the repairs some of you people are doing, I’m green with envy.
As for moving it around, yes, with your hitch it should be no problem. Cost a fortunate though if you’re ferrying it to the island! I practised backing up in empty parking lots. I like the feeling of pulling into a campsite & backing my
trillium in with ease. I actually received a standing ovation from a neighbouring campsite! (The dinner invitation was an added bonus)
I was born on Vanc. Island but live in Ontario now…..I cover my
trillium with a tarp & clear off snow when it gets too heavy. I leave her bare in summer & we get a lot more sun that BC. The sun sail sounds good though, especially if you have no trees for shade & are on pavement.
As for the garage, find out the height of your trailer & measure. My trailer is 4 inches too high for my garage but I’ll be damned if I’m going to remove the
tires every year, so I leave her outside. That way I can give her a wink & a pat when I walk by….or shovel the 3 ft of snow.
Good Luck! Having a trailer opens up a whole new world of adventures, whether near or far.