Sportster transmissions come out without splitting the case. Just pull the primary apart and unbolt the "trap door".
A Evo Sportster is a very reliable bike, as in "Toyota Truck" reliable. What did he do to it to grenade the motor in 60K miles? 2K is too much. You can buy good running bikes for that. 1K would be pushing it. Looks like it does have a lot of chrome and custom stuff, but that can just be more junk too, depending on the quality of the aftermarket parts.
44, the one you're looking at is an Iron Head Sportster. I would run away from that, screaming into the night. If it was free, it would be too much. A friend of mine built his shop from a 10 by 10 stall into a HD dealership by being the only shop around that would work on those. We counted 23 of them lining the walls waiting for various parts once.