A light duty F250 was available in 99. Looked just like the F150. It didn't make it past 99 though.
If you go with the Super Duty, you can't go wrong with the V-10. Very reasonable gas mileage and plenty of power for what you are looking to do. The 5.4 gas might get the job done, but from what I've read, the gas mileage isn't any better than the V-10 in this application so why not enjoy a bit more power?...... (Of course the real workhorse is the diesel..... if that is what you are interested in. Just plan on spending big bucks to get it initially, and spend more to care for it over its life.)
Overall, I'm happy with my 250 Super Duty. Only complaint is the 4.3 gears are a tad low for highway cruising. (Will fix with larger tires one day!) I'd certainly recommend the 3.73 gears unless you tow heavy, (or never leave the farm!)
Matt
99 V-10 Super Duty, Super Cab 4x4