If you're thinking a nice, used 5 year old in the $20 - $30,000 range, I think you'll have money to spare....depending on what you're after. On the good side, you don't take the hit on depreciation and if there are any OEM major problems, they've likely been remedied by that time.
The downside is that you have no idea what, if any, routine maintenance has been done by the previous owner. Most dealers aren't going to offer much of a warranty, if any on a 5 year old trailer. Problem??? Maybe.
If this is something you intend to keep for several years, I would be of the opinion that new is better. Both our HTT and TT were bought new and we didn't mind taking the hit. Didn't LIKE it, but could live with it. By the time the trailer is 5 years old, the warranties on appliances, A/C, furnace, etc have most likely run out. You could have a lot of things to replace in the near future. Unless the tires have been replaced by that time, those will be first on your shopping list for $500 or so.
If you're ready to spend that amount of money, I'd shop new, specifically RV Wholesalers and RV Direct for a baseline. Both companies are good and offer excellent prices. If you choose to by locally, you have a bargaining tool. Happy shopping.
Trailerless but still have the spirit
2013 Rockwood Ultra Lite 2604 - new family
2007 Rockwood ROO HTT - new family
2003 Ford F-150
4 doggies - We support Adopt/Rescue.
Sam, you were the best!
Cubbie, Foxy, Biscuit and Lily - all rescues!