Hi, having just done a similar transition, I can tell you the
learning curve is a little bumpy, but doable.
I recommend taking a sailing class on the same exact vessel you plan to buy.
That helped a lot.
Take it slow. Shop around, and be sure you will be comfortable handling the size of boat you buy.
Consider
buying, or
renting a 30ft, and doing coastal cruising to gain experience.
Don't be afraid to
motor, take the sailing slowly in light winds.
Keep
marinas close at hand to pull in for
repair, or wait for good
weather.
I'm in the middle of getting my
new boat back home when the virus hit.
Piloting a 40 ft
Catamaran, turned out to be both a handful, and easier than I anticipated. Kind of like driving a small floating tennis court.
Cost to operate goes up dramatically with size.
Good luck. Should be some great deals soon.