Yes I'm going to purchase a gently used one and a cheaper model. I do not want to have buyers remorse later and make a financially bad decision. it is after all my first motorcycle.
If you're buying a Harley then the good news is the resale on them is crazy. You'll take little if any loss on it whether you sell it in months or years. The models change very little from year-to-year, so the resale remains pretty high unless the bike has a lot of mileage or isn't kept in nice shape. There are some exceptions, like on the Big Twins when they changed from the 5 speed in 2006 to the 6 speed in 2007. It was such a big change that it did hurt the resale of the 06 and earlier models a bit. But it's pretty uncommon for them to make big model changes like that.