I had a few regular cab trucks and they meet my needs at the time. My most recent truck purchase was an extended cab 4WD because I needed it to transport elderly parents in snowy conditions, in addition to myself and my wife, which not the situation you are in. Get what you need or want and don't worry about other opinions.
As to a HD truck vs. regular duty, if you are in a situation with your farm where you need to haul, there is never too much capacity, while there can be too little. If you aren't worried about 20% additional fuel usage, get what you want. With such short distances to drive, I don't think fuel usage is much of a consideration.
I looked up GM Employee pricing on the truck, which used to be approximately invoice less holdback and incentives. You should be able to get the truck for about that price. A good deal on that truck would be list minus $3200 and less the $500 incentive currently available on the vehicle for a total $3700 discount. TrueCar indicates the truck should be available in my area for a similar discount.
I'd offer $35,300 for the truck, and ask them to throw in the tint. I'd increase my offer by their cost of tint if necessary.
And I wouldn't settle for a Honda minivan with a bed, but that's just me.