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First off, you bought a Rover. Expect for it to be somewhat less reliable than a Honda/Toyota and cost more to repair. You need to begin investigating local independent import shops to find one that knows and loves the Rover. You'll need to drive past and look to see if they have any in their bays or lot and talk to them at some length. "Yeah we work on all of 'em" is a bad sign.

To your specific: it's probably not your transmission. If it were low on fluid and slipping, you'd have been on the tow hook already. And warming up a slipping transmission doesn't make it not slip. It's likely there is a malfunction in the engine management system relative to coolant temperatre. Do you have any lights displaying on your dash- ones that shouldn't be there? Nonetheless, a good, proper drain, flush and fill on the transmission, differentials, etc is definitely something you need to get on once your problem is fixed.

On oil change, the cartridge filter is probably a bit more idiot proof than a spin-on. At least you won't have some mouth breather double gasketing it. But I'd leave that to the good, qualified independent you're going to find. The oil and filter are more important that who's changing it. Use the best you can get, which is a premium full-synthetic. I use Motorcraft filters in my Ford diesels, and BMW filters in our BMW's. I'd suggest a Rover filter for yours. For everything else, the Purolator Pure 1 is a good choice and if they have it for your truck, I wouldn't lose sleep over using one. The One, not the cheaper piece.

Anything can break. My first real job was repairing brand new GM vehicles as they rolled off the truck at the dealer. But $1200 for an oil cooler line and a thermostat--- something's wrong there. These Rovers use a higher-pressure cooling system- it's a BMW design that somehow remained after they sold the Co. They are notorious for parts failure, especially the molded plastic stuff. When my wife had her E46, I replaced the ex tank every 2 years AND carried one in with the spare tire.
 

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One other thought- do you notice the car pulling to one side or another or steering funny? Do you smell anything odd? Do you notice after driving a while unusual heat coming from any wheel(s)? A stuck brake caliper or two can cause this sort of issue. Your engine isn't going to make max power at cold startup and a stuck caliper can put enough force on the driveline to slow you down. Once the engine gets up to power and the brake rotor heats to the point of doing very little, the drag will seem to disappear. Probably won't stop all that great though.
 
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