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Biggest and most difficult move?
I don't know. It seems like all of my earlier-in-life moves were the kind that could be accomplished in a few car trips. This is prior to the years of having my own furniture, etc. In later years, I've always managed to attract either friends who could help in some form or other, and nothing particularly nightmarish comes to mind. Then I had a few work related cross-country moves that were paid for and executed by the big moving companies, so as huge an undertaking as those were, I can't say they were personally difficult. (It's really great, in fact, to have all of the difficult stuff accomplished by a staff of people you're not even having to pay for. Oh yes indeed it is.)
Okay, I'll pick this one: The move from my first place in Danbury (a very decent two-story townhouse type of apartment) to a rented house a few miles away had to be largely accomplished by me, and in somewhat of a rush situation because the apartment had just been sold quicker than expected. I had local guys move the furniture and a lot of large items, but I remember a hectic night from Hell when I was schlepping several carloads of the last stuff over there myself, and I thought it would never end. Nothing noteworthy about it, just that it was a time when I could have used a lot of help and had completely failed to plan for it.