Been going there for about 7 years. My preference is to rent a place in Evarts. I've done the Putney side thing and don't mind it, but I like the availability of food and fuel over in Evarts. Just don't jackass around or give the local PD a reason to stop you. I've been hassled one time by a local youngbuck LEO about 4 years ago and he got his ass reamed by his superior right in front of me. Basically he got told don't **** with the people that bring money into your town unless they do something blatantly stupid. We rent from the sheriff so if you do that and stay at one of his places, you're pretty much guaranteed to lessen your chances of being messed with by locals or LEO's.
More than enough wheelin for 3 days or more IMO if you keep your rig in one piece.
We usually do it a little different, but this is how I would probably tell a newbie to do it for the first time at Harlan.
Day 1: Go hit the stuff further away. Its a good trail ride to familiarize yourself with the place. You'll see a lot of trail names and intersections on the map this way. Hit Mason Jar and Lions Den then work your way back down toward whatever side you camp on.
Day 2: Make the climb up the mountain. There are a bunch of trails that pretty much link together to get you from the Evarts trailhead to the Middle Rock Garden. Pinball, Railbed, Fish Fossil, Lower Rock Garden, Killin Time, Profanity then shoot over to Middle Rock Garden and Grapevine.
Day 3: Start near the Lower Rock Garden again then head over to Whitetail: Steel Hill, Pony Hill, Lower Damnation then drive over to the bottom section of YourTurn (top was wicked last time we were there in March), Crawfords Cry, TROUBLE, Whitetail Crawl then come back down the mountain.
Days 4-5: Assuming your **** is still in one piece then grab the map and go find anything you haven't hit yet. Days 1-3 will get you over most areas of the park and hit all the must do trails IMO. Finish it up with what I consider the "consequence" trails like Little Jagger and CreamPuff.
You can cover more or less each day depending on the size of the group and how much **** you blow up.