Welcome to part two in my Mobility series!
I'm going to discuss trucks here. I don't think that you need to buy the truck first and the trailer second, or the trailer first and the truck second. I think it's a personal preference as long as you aware that whatever you buy first will dictate in some ways what you buy second.
There are plenty of truck options out there.
You can get something that will match every single hauling need you'll ever have in the future. If it's in your budget. Keep in mind that bigger trucks mean bigger repairs, bigger gas bills, bigger parking spaces. Or you purchase a truck to meet your immediate needs with good resale value and plan on upgrading in the future.
If you're on a budget older is fine but you need to have a qualified mechanic helping you make the decision. you might find yourself getting a bigger older truck because today's technology advancements mean smaller trucks are capable of towing more. Older vehicles all come with a certain amount of wear, tear, rust, and repairs but an older well maintained truck can be a great deal for someone, especially if you think you might upgrade in a few years. What does the inside and outside look like? An older truck with minimum rust means someone cared about it enough to give it a bath and if they gave it a bath they probably took care of the engine and didn't ruin the suspension by off roading. Maybe.
One problem I ran across is boy toys. Trucks modified for "looking cool" and not doing things that trucks should do (in my opinion). Those tires are really expensive to replace and you're going to need a drop hitch to accommodate that lift kit. Does this beast have mufflers or can you hear it coming 4 miles away? Has someone taken it off roading?
When buying on a budget you might have to make sacrifices. Crew cabs and 4 wheel drive trucks are very desirable and thus having both is a hefty price tag increase. Do you want the storage and extra passenger space or do you want 4 wheel drive for mud and snow? A little bit of rust for both 4 wheel and crew cab? Or lower mileage for standard cab?
Rust is another consideration when buying used. Rust on rocker panels is pretty much a given and rest left unchecked can eat into the door and frame of the truck causing costly repairs or it to be unsafe while towing. Are you willing to accept some rust to get other things like low mileage?
In the end when shopping it all comes down to must haves, compromises, and most important budget. I think that budget shoppers MUST have someone qualified looking at the truck beforehand. Issues you might even notice can be thousands of dollars in repairs before it's safe to tow with.