F150 (1500) or F250 (2500)

If you don't need a heavy duty, spare yourself the potential issues.

Half tons these days have a nice towing capability.

Yes, I own a 2500.

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Medium or high trim level?

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i'm not sure here, but i've traded 3 high trim levels at about the same age/mileage as you are assuming and I've done fairly well

i recently bought a lower end F150 just because I realized I didn't need most of the higher trim level items

i hope when I trade in this one in 2.5-3 years that it wasnt a mistake

in general, i think driving that many miles a year, you are going to drop about 7-8K a year

i do think options like 4x4 and diesel (on a 2500) are very good for resale

If you lease you'll get killed on mileage.

I have a 2017 F250 6.7. I could probably get buy with an F150. I have a 70 HP Kubota I pull 15-20 per year. Its more about stopping than pulling for me. I like the engine brake feature on the 6.7, better brakes and heavier truck. You can get a 5yr\100K mile extended warranty through Flood Ford for $1800 which is a good deal.

KLSU I am holding out for that big 7.3 gasser as my next ride. Currently in a 2012 diesel with 124k miles but will be switching to gas next go round. Fuel and maintenance is considerably more with a diesel. Not to mention that extra $10k sticker price