Third Gen Head Gasket Purchase

I've been looking for a third gen for a beat around toy for a minute. I'm on my second XJ and I love them but the 4runners have been calling me for about a year. I had a little money set aside for a small fishing boat to mess around with and saw a 2000 that needed a head gasket with 248k on the clock. The rest of the truck is in great shape. He alleges that it just got warm but didn't overheat. What I'd do is take my boat money and buy the 4runner. Sell the beater XJ to pay someone to do the head gasket and do timing and WP while it's opened up. A reputable shop warned me that if the heads need to be machined with that kind of mileage then there's a solid chance it's going to burn oil past the rings with the higher compression. I'm also finding that the estimate of $1,000.00 to do the job was very optimistic. My XJ is listed for $1,500 but probably won't bring that.

I guess my question is, should I be that concerned about the ring issue? This is a chance to finally get into a nice 4runner as a beater that's already lifted and had the bumpers pulled for about half of what it would normally cost me. I've watched the job on YouTube by WorseThanChiggers and I'm almost feeling adventurous enough to do it myself over an extended period of time. It's definitely above my skill level. That said, I gotta believe that if I screw this thing up I can get $800 for a 4runner that needs a head gasket.

What sayest the mob? Pass or pick it up?