Not necessarily an Osborne
I had an Osborne as my first computer, it was a very handy computer for the year. Once PCs hit the market it was redundant; the machine I've still got from that era is a Corona Data Systems luggable -- that's got the larger screen.
I've never done much business travel but one really interesting visit was on short notice to Israel. I had to carry a prototype and some testgear with me; that mean I was carrying a small case with 'things' in it, including circuit boards sporting both red and blue wires. The case never really recovered from the probing that El Al security gave it. In fact they were so interested in it that on the way back the security agent spent so much time on it that the next person's toy, complete with tool kit, was waved through.
(That in turn reminds me of my student days, back when I had a 4 and half inch standard ball float that I'd painted black with the word "Bomb" on it. Went with the cloak.)