cheaper vs less problematic
Forget about trying to get your money back when you resell. Just get the boat that feels best to you now. You might end up owning it longer than you think.
And don''t be too concerned with the "extras" one boat might have. Most of these things can be added on by you when time permits.
Sailboats are not an inexpensive habit. Over the next year or two you could easily drop an extra $1000 or 2 on sails and other incidentals on either of these boats you are considering.
Dive in and have fun.