I daily drive a square and have done so off and on for years... If it tells you anything, I stopped daily driving my Mercedes CLK coupe to drive my c10 instead, but that's more of a mood and a preference thing, don't read that into comfort or handling
Here's what you need to ask yourself in my opinion:
#1 - How much do you drive? I bet the square with a 454 non O/D is going to get half the gas mileage of the 2008 on a good day. Maybe even less. Realistically figure gas around $4/gallon in the very near future, it creeps up every year and if the global economy picks up, esp the chinese slump, they will find an excuse to pop it higher to the $4-5/gallon range.
#2 - Where you live get an insurance quote before assuming it'll be cheap. Part of what they look at it rate of injury and property damage when a truck is in an accident on most general car insurances, so an old square can be expensive if you cannot qualify for collectors insurance (another daily vehicle, stored in garage, etc) It is less if you are garaging in a rural area, but do your homework.
#3 - Expect repairs. The payment will be gone per month, but plan to set aside maybe $75/mo to your repair account so you can pay to fix as things break which they will on an old truck. Some months you won't use it, but that makes up for the months when its a $350/400 bill.
#4 - Think of your travel habits and where you need to park. A big truck like that isn't city friendly and can be hard to park, more so when idiots in their prius who never drove a big vehicle pull in stupid near you and make it hard to leave not realizing you do not have a cab forward wheels to the corners design...
#5 - Finally comfort. The square is a truck is a truck is a truck. Will it bother you to feel bumps in the road and potholes? Does wheelhop bug you? Are you willing to relearn rain driving a bit if you aren't used to driving a square on the highway? A LWB with a heavy 454 up front will be very very light in the rear, somewhat prone to breaking the rear tires loose in heavy rain depending what part of TX you are in... or snow for that matter. There is no traction control or the like in the truck which you may have gotten used to. Also, if you do live in an area that gets cold do you mind sitting for a few minutes on a cold morning for the truck to warm up before driving? Unlike FI that carb is going to need a few minutes to get going on a cold morning...