Sabre sailboats are pretty highly regarded so you've got a good one there.
As Dave suggested, you need to be able to "hide" or stow the lazy jacks when raising the main sail. See if you can find the control lines for your Lazy Jacks - you should be able to loosen them. If not, consider replacing the Lazy Jack sail control lines with bungee cord line. This way the Lazy Jacks can be stretched up to the mast and fixed there so they are out of the way of the sail when raising.
If your main sail has those plastic sail slides to hold them in the slot I can tell you that they do wear down and will pop out of the sail track at the most inconvenient times. You can get new sail slides from Sailrite (and other places) which may require a little sewing to attach them to your sail. If you don't have one I'll recommend the Speedy Stitcher kit: Speedy Stitcher Sewing Awl Kit - Online Video Instructions for the Sewing Awl
Sail slide (3/4"): Slide Nylon Internal Flat 3/4"
It is quite important to get the exact size to fit your mast track.
Getting from NY to Port Washington is an easy train ride. Less easy by car.
Which marina are you keeping your boat in now? Most of the marinas there are about 1 mile away from the train station.