1961 "Les Paul" badged SG Junior, though I don't use it these days. Marshall Plexi Lead from around 1969, still works but retired.
I do use a Jen Cry Baby Super I bought new in 1979, though it's had replacement switches and pots over the years.
Electronic stuff aside, my oldest piece of kit in regular use is a mid 19th century fiddle.
As for software, no idea really.