My oldest and favorite guitar is an old Martin 00018. I use that for most song circles, jams, and gigs where I really want the guitar to sound good and don't need to amplify it.
For my everyday work (playing and singing at retirement and nursing homes and senior centers, etc.) and whenever I need to amplify the guitar and don't think a mic will work well, I play a cutaway acoustic-electric Sigma (roughly the same size and shape as the Martin).
I like direct-ins for amplifying my guitar, since I move around a lot when I play and sing, and it's really hard to keep a guitar mic positioned properly.
I also have about 8 more guitars (a Martin Backpacker, a 3/4 size Ibanez, 2 dreadnought style flattops, an electric, an Takamine Jasmine cutaway acoustic-electric nylon-string, an Alvarez that's the same size and shape as my Martin but needs a peg replaced, and an old Gibson LGO which is nice to play but doesn't stay in tune very well, and another Sigma which I play when I'm in San Diego).

The Backpacker has turned out to be quite convenient for keeping by the computer when I'm working on sheet music or lyric/chord sheets. The Ibanez is great for travelling when a full size guitar would be too unwieldy. I haven't really learned to play the electric yet, but I want to. Several of the others I'd like to sell, but I haven't got around to it yet. It's nice to keep one or two of the cheaper guitars on stands in the house, though, so I can grab one when I want to plunk out a tune. (I like to keep the better guitars in their cases so the cats can't knock them over.)

For fun, I play at jams and song circles in Seattle, Portland, and (a few times a year) in San Diego, as well as at the various folk singer gatherings in the Pacific NW (RainyCamp, SunnyCamp, Camp Runamuck, Singtime Frolics, etc.) and at NW Folklife Festival in Seattle on Memorial Day weekend.

Come play music with us "south of the border" sometime, JJ--OK?

Genie