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Fantastic story! I think I've heard a slight version of it. I don't remember how you stopped and picked it up again. Imagine if you would have not found that DVD and suggested to watch it again?!
You might never have:
1. Watched Everwood ever again!
2. Dated Tom/Harold.
3. Met cool me!
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I know, right?! It's crazy to think about that! I would have missed out on seeing one of the greatest-written and greatest-acted shows
ever, dating my dream guy, and meeting one of my best friends.
I'm so glad that Fate stepped in that day and made me find that DVD!
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As for when Harold was my favorite older character... it was when Harold and Andy first met, Harold was ticked at where Andy parked, Harold insulted where Andy was setting up his medical practice, Harold was pissed at Andy for stealing all his patients, Harold was basically obsessed with the Great Doctor Brown. 
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That scene truly showcased so much of what we have all come to love about Harold, and about the Harold/Andy dynamic. Truly the perfect introductory scene! Berlanti, Amandes, and Williams = genius.
Oh, and in "The Pilot", when all of the patients were lined up at Andy's office and the one man said "Thanks, Mr. I-Can't-See-You-Without-An-Appointment" and it's supposed to be a moment of victory for Andy and for the audience...I was probably one of the few that felt bad for Harold and kind of wanted to wipe the satisfied smirk off Andy's face.
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I also loved these quotes:
Even the couple of Andy/Harold knew Tommy and Madison sucked.
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I love that part too! I loved all of the Andy/Harold bar scenes. Man...they should have had more of those in season 3 and 4; in fact, I don't think there were any at all in those seasons. And it was blasphemous in season 3 when they showed Andy and Jake meeting and taking medicine at the bar.
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LOL! I loved the interaction Harold had with Andy and Edna so much. Amandes is such a captivating actor. I noticed him immediately. Same with Emily. They both have this eye catching acting that you can't miss. It really is the acting for me. Tom just brought it and I noticed!
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Ha! The Harold/Edna scene!! YES. I love them together. They play off each other so well since they are both similar and opposite at the same time. Wow, that'd be another thread for me to revive--or create if it hasn't been already.
And you're definitely right about the acting. Harold could have easily been a one-dimensional character, someone like Taylor Doose, but obviously Berlanti never intended that for him and thank goodness that they got an actor with such a wide range, extraordinary in both comedy and pathos, to bring this complex character to life. I really don't think too many actors could pull off the task of making Harold kooky and crazy, uptight and snarky, and warm and sympathetic all at the same time.