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k the upgrading would be later down the road. What tranny would be in the f350 crew cab being an auto trans for the obs
E4OD in mine and I think that is true until the SDs came out - not positive there. Lots of people swap to a standard but I like mine after I put in a shift kit. Unless you plan to make stupid power it should be fine. In the beginning you will spend time fixing all the little things a 16+ year old vehicle will need and then changing fluids and correcting all the things the PO let slack the last few years of ownership - that would be my guess based on your price range. If you can get the bank to give you 13k you won't have as much of that to tinker with, but then you'll miss all the fun!
Lots of opinions on oils and most of them are just that, opinions.
Find something your comfortable with spending money on that you will be able to get regularly. Some guys like synthetic, some of us run conventional oil. The 7.3l will be happy with either as long as it's clean.
Really, most any diesel rated 15w-40 will work. Some like Rotella, but I've heard that it doesn't hold up to the high pressure the High pressure Oil Pump uses. The 6.0's have more issues than the 7.3's though. I run Amsoil myself, others use Schaffers Oil, some Delo 15w-40, some run 5w-40. If in doubt, Motorcraft that's rated for the PSD will work just fine. Do not use any oil additives. Really, just use good oil and filters, and don't mix anything else with it. Lucas oil has even come out with a different oil additive specifically for PSD's because their old formula was causing problems. If you keep it changed like you're suppose to they'll do just fine.