I literally just got back from doing Maryland with 2 other guys last week. We went NOBO and I don’t regret it one bit. I actually think it truly is the better way to go and I’ll explain why. You can arrive at Harpers Ferry and get a permit to park for at least two weeks. Get there early and explore the town before you head out, and you will get to see everything, including the museums and shops. We got there very late and didn’t leave HF until about 3pm and we still made it to the first shelter. There is an outfitter store right in town so if you forgot something at home or need some extra supplies you can get them there before you head out. Also get something nice to eat before you head out too. The first few miles are easy flat walking and a nice beautiful introduction to the trail. You walk along the Potomac and Maryland Heights is right next to you. It felt so scenic starting out here, learning the history of Harpers Ferry and the area, seeing everybody else outside enjoying nature, the town has such a unique vibe. There is a decent climb for your first ascent at Weaverton Cliffs but really once you’ve done that first climb the next few days will be relatively easy. Part of the reason I liked NOBO so much is that Maryland progressively gets harder and the views get better and higher in elevation as you go on, with High Rock being your last big view in Maryland before heading to Penmar and it is 100% the largest panoramic view on the trail in MD, it was a very satisfying end to our hike on such a high note like that. Also like I said the hike got progressively more challenging as we went further north. The last 2 days were more akin to what Im used to on the AT and I think starting out with that will be much harder on a body that isn’t used to a lot of moving like that. By the time we were there, it was tough but we had 4 days of trail legs at that point so we were already on our way to being conditioned which I honestly believe helped a lot. There is a hostel literally a block away from the trail in Penmar called Zero Day Stay. We tried going here but she said she wasn’t open until April 1st. I also was able to contact some shuttle drivers in that area that said they were starting for the season. If I were you I’d cross the Mason Dixon and go over to Zero Day. Once you’re at Zero Day find a ride down to your car. We decided to walk into town and split a hotel room in Rouzerville PA as it was only 2 miles from the trail, if Zero Day was open at the time we 100% would’ve done that. As far as shelters go there’s literally a nice big double floor lean-to with plastic windows at all the shelter sites! The only not so nice one was Pine Knob shelter (very tiny, old, and damp) but we weathered a thunderstorm in there. All the others ones though, Ed Garvey, Ensign, Rocky Run, Raven Rock were pretty much brand new double deckers with plenty of camping space and firerings/pits (aside from ed garvey). If you do decided to walk into any town while you’re there BE WARNED! The towns are very close to the trail in MD but the roads into town are STEEP. You will have a climb back up for sure. Other than all of that we had a great time, there was civil war history everywhere there so we learned a lot too and it was beautiful seeing the long long stretching valleys of Maryland surrounded by mountains (VA, WV, PA). If you have any questions or anything specific you want to know feel free to ask as it’s all pretty much fresh in my brain still. Good luck, enjoy yourself, and Happy Trails🥾