On the Speedster you may want to consider your mechanical options. I owned a VS for 3 years and had a good experience with it, and with Kirk.
On any buy, I would get the front discs as a minimum & depending on your budget you may want to consider the discs all the way around with a wide 5 pattern. Make sure it is an IRS car. I didn't and used a camber compensator on swing axles and it felt good to me, but I undestand the IRS cars handle better. I haven't looked at the VS options list lately, but make sure your top and (get) both tonnaeus in canvas. Get both side mirrors. My experience with engines has been limited to (2) 1776s and a 2110. One of the 1776s was a boat anchor, the other is running strong after 30,000 miles of duty. The diffrence between the two? I had the second one built with a balanced crank, and all good internals, a good cam, and carbs. The 2110 that I have now (7,000 miles) is a leap in HP and torque and I love it. Many will tell you to buy as much horsepower as you can afford. Or, pick a size and then go up two. But that's something you will need to work out on this or another thread with input from current owners of VSs. Some prefer the 1776 with ICTs for an easy to maintain car with credible HP.
Good luck, and have fun. Oh, get the VS luggage rack. It's fairly cheap in cost, but works for those weekend trips. I think it looks sharp, but you will get a variety of opinions on that.