Older bigger pickup or newer and smaller?

So Veeky Forums, I currently own a jeep liberty and I need to purchase a pickup truck for work in the coming months. I originally was looking at a 2006-2008 dodge dakota, but now im looking into maybe an older 2500 ram or a ford f250, maybe around 2000 to 2002 year wise. What is your suggestion Veeky Forums? Should i go with a newer mid sized pickup? or an older larger pickup? Or do you have any other suggestions? Mainly i need a truck with 4 wheel drive, automatic transmission, a tow capacity of atleast 5000 (looking more to get a 6000 capacity) and a good sized payload, extended cab or crew cab is a must. Looking to keep this under 10k, but closer to 7 or 8 if I can. Thanks in advance guys.

Tacoma. Any year.

Why? They aren't going to supply you a work truck?

I own my own business, so i have to supply my own work truck haha.

We'll if repairs are tax deductible I'd get a new 6.7 powerstroke.

Otherwise I'd get a 7.3 powerstroke or cummins 5.9

Under 10k

like a brand new 2016 truck? thats way too much money man. im not making enough to afford a brand new truck

OK so wait a while and spend 12-15k on the 7.3 or cummins

i cant afford a new truck at all, im shooting for around 7k or 8k, 10k is if I found a great condition truck that was an absolute steal at 10k.

The main purpose of this thread was just to see if people would rather purchase a newer mid sized pickup, or if people would want 10 or 15 year old pickup truck that was a big heavy duty truck of the time. The main thing keeping me away from the older bigger trucks is the maintenance costs and repairs, but some people say the older trucks have alot less too them, so maybe itll be less repairs. im just seeing what you all think.