One thing I really do not like is having to pay for hotel room when I arrive..why? I would much rather pay for them in advance if just because I like to save time of checking in.
The feature of prepaying via Hotels.com is awesome. It totally frees up that last minute charge of extra taxes and usually the best thing I use to like about Motel 6 was the prepay option too until it gets difficult.
My suggestion is to prepay your vacations as much as possible from airline to hotel to car. One thing I had not been able to get under control is the food and beverages costs. I can prepay for sailing, horseback riding and even wine tasting but a lunch date? Nope.
How to fix that? You guessed it ...Gift Certificates / Cards then you can just pay gratuities. If your hotel room does have a mini refrigerator use a popular grocery and make dinner in your room ( its perfectly okay to do that by the way ). Then you can change before heading out to the movies and dance clubs.
Oh! Insurance. I will address travel insurance in a different post but the biggest thing is to make sure your auto policy allows for rentals and your health insurance has ER care. Its not an easy thing to address but if something happens to you while you are on vacay but your not traveling overseas you should be good.