[MENTION=219088]GogDog[/MENTION]; was just in a similar position to you, just pulled the trigger on my new '18 silver TRDORP. Personally I came from a 4x4 offroad F-150 on 275's; never felt the need to lift it.
Bought the 4runner and figured the same thing. The truck sits pretty high stock and the 265's really do fill out the wheel wells. But its been almost a month now, and I'm on my new BFG KO2s in 265.. and I'm gonna need to lift this thing at least a little. Parked next to a Sierra and it made my runner just look like a minivan.
Personally, i won't lift it more than 2". From the pictures i've seen, the 265's will still be plenty large enough. But if you have a tickle somewhere in the back of your head saying "huh i'd kinda like a lift.." you should just plan on it from the outset. If I knew three weeks ago I'd feel this strongly about lifting the Runner, I'd have gone with the 275's just to stand out a bit more.
Re resale value: Discount tire offered me $50/tire for the dunflops. I'd guess you'll be able to craigslist/ebay/local runner group sell your wheels and tires for $600-$800; as devastatingly stock as the ORP wheels look, they are actually pretty damn sharp wheels and I've seen a lot of older models rolling around on them.