I am looking for my first pop up, and seem to find that the dealer prices are 25-50% cheaper than the private sellers. This seems odd to me or is this normal. What are the benefits of both and how do I "test drive" a trailer?
I am assuming that the dealerships models (gently used) are trade-ins, and accordingly priced to sell. I too have recently seen that some of the dealerships models are lower in cost than those of private sellers. I think that's a good thing. It might help the economy somewhat as to financing if those trade-ins are sold fast.
As to what to look for when buying a used trailer....you have to inspect it from the tires up - be sure the wheel bearings have been re-packed/lubed recently, brakes adjusted, all the amenities (appliances) work, roof in good condition and sealing well.
You might want to read "Natasha's Camping Site" for good information on buying a gently used popup and what to look for.
If buying from a dealership, they may provide some type of warranty - but you will need to check. The private sales don't have that option, and little if any of the factory warrantied items allow for transfer of warranty.
The dealer said they would go over everything in the pop up to check that it worked and teach us how to use it. It was a 2005 Starcraft 2107 for 5000 with air, which seems a good deal but I am probably over cautious. Do the smaller pop ups sell better or the larger ones? We actually may need to look smaller yet or get a bigger tow vehicle but with this economy its scary to buy anything.
The dealers have more than one trailer to sell and may be nervous about carrying large inventories, so they're making deals.
Here's one on CL for $4,500 that has everything you seem to be after and looks brand new. So depending on what you settled on for price, you're putting $500 or more into your pocket as compared to buying that one from the dealer
http://akroncanton.craigslist.org/rvs/1115695454.html
(http://i569.photobucket.com/albums/ss139/fire938/287012_1.jpg)
Also, note how "small" the camper is, and what he's towing with (because I know you're considering what you're going to do about a TV).
Here's another example, and with an asking price of $2,500 you now have $2,500 to put toward a TV
http://akroncanton.craigslist.org/rvs/1101730745.html
(http://images.craigslist.org/3nf3k63mdZZZZZZZZZ93v256f8f695f931c74.jpg)