I have been playing guitar for 51 years. My starter was a 1934 Montgomery Wards guitar that my father bought when he left home (at age 14); that action was about ˝ inch! Many bloody fingers for that time!! Then for confirmation in 1963 I received a handmade guitar from my parents. Two brothers began making guitars in the early 1960’s. This was the second one that the older brother made, and he only made nine. I gave this to our oldest granddaughter three years ago; it is the only surviving guitar from that line. Those two brothers taught me how to play. They were (and still are in their 80’s) superb guitarists.
In 1964 I paid $400 for a 1956 Gibson, thin body, double cut away with single pickup—bright cherry. One of the smoothest playing guitars ever made. I played that in taverns, dancehalls, etc. beginning in 1967 (yeah they were lax about age then). The brother who made my guitar also played rhythm guitar and would sing, while I played lead on the Gibson; then he would switch to the fiddle and I played his flattop (one made by his younger brother).For my 21st birthday we played at a tavern doing that kind of thing. When we finally left at 5:00 AM, I made $3 and he gained two quarts of dill pickles.

It was the only time I ever made money on playing guitar.
I kept that Gibson until 1992, when I sold it so that I could buy a handmade guitar by the younger brother (he has made about 225, plus about 175 Mandolins). It cost $1300 at the time. Today his guitars sell for $3500, and Mandolins for ~$6500. I have played this in church services, weddings, family gatherings, etc.(no more taverns!). When I do play with others, this guitar stands up well against any Martin or any other top-of-the-line flattop guitar. In the early 1960’s he had made a few classical guitars, and one was played by Segovia who commented that it was one of the best he had ever played.
So, right now I have one guitar. My preferred style of music is bluegrass (flat-picking) and old (pre-1965 mostly) style country music. Over the years, guitar playing has been one place of solace for me, especially in my teen years. But even now I can begin playing to relax.
(Thanks for starting this thread)