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How Many Basses at the Live Gig?

I'd say (like many others) to bring 2 (one for b/u) but if you really want to play both and take advantage of their tonal attributes I'd think about how you'd manage the changeovers. You want to keep it as seamless as possible, ideally changing only once. Keep it simple.
 
I bring a primary and a backup. They're identical, so I usually flip back-and-forth between them. from gig to gig.

But if it's worth my back and slowing down the show to really entertain the 1 or 2 people in the audience that might care about what my bass looks like or sounds like, I'll bring more. (Read: I'm just bringing the 2 basses.)
 
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I’m mostly a recording hobbyist, but a songwriter I respect asked me to play an extended set with him, and I jumped in. I’m having a great time woodshedding the material. Feeling some rare musical fulfillment.

There's no 'right' bass for a song. It how you play, not what you play, that matters. Play whatever makes you happy, be it one for the whole set or one for each song. Folk will, though, wonder why the need to swap them about. I've known only a few guitarists swapping mind-set and no bass players.

First few times running through the material, I was on my go-to P with flats, but pretty quickly one tune started to beg for the fretless. So I got that locked in; sounds good.

And then another—90’s R&B vibe in A-flat—really wanted the 5-string with rounds. Done.

Last night, as I was packing up the 3 basses for today’s rehearsal, I thought “Am I insane?” I want to get the perfect sound for each song, but am I going to look ridiculous up there? Like I’m in an 18-song flex all about myself?

It was shortly after that thought that I decided to refresh myself on something real quick and, with the P packed up, I just grabbed the Mustang off the wall and…smh…now I need to have that sound (Mustang, La Bellas, foam mute) on this one song.

Is 4 basses over 18 songs a ridiculous look? Will I hate myself at the end of the night—or more specifically, will my 55-year-old back hate me? For you guys, what’s the most basses you would bring to a gig?
 
I always bring two basses. Since I own 24 lefty basses, almost all of them in the rotation, it's a tough decision. Sometimes I used to wonder, 'man, if I'd only brought the red Precision.' Since my gigs have radically dwindled from every weekend, with week long blocks of casino gigs far out of town, to maybe, and that's a definite maybe- one weekend a month. I don't play a lot of my instruments on gigs now.
I had my 100 year old German upright fall over and break on a Western swing gig about 20 years ago. Good thing I brought an electric bass with me. I'm a Luthier/ repairman, and had the upright back on the next nights gig, no problem. LOGIC, should dictate that you NEED to bring a minimum two basses to all gigs. Why? Because of my experience- you really do not want to be an hour drive from your bass collection, and have some major or even minor failure of the single bass you have on the gig that night. I used to sub for a bassist on a Lake Tahoe paddlewheeler. Imagine, if one of the tuning machines broke in the middle of the lake. I HAVE had a Schaller M4 break on a local gig once! Try playing on three strings sometime. It's just using common sense, and the law of Mr. Murphy. Sheet happens, and you'd best be prepared. More than that, and you switching basses all night will annoy everyone in the band. Trust me, I know this well.
On gigs out of town, with nights in hotels, I bring a Luthier's 'road kit' as I call it. It contains: A small soldering iron, solder, diagonal cutters, needle nose pliers, a worm gear adjustable wrench, several screwdrivers, a truss rod wrench assortment, some sandpaper, a file or two, steel wool, Toothpicks (for screw hole dowelling) medium SUPERGLUE, and a few other things I'm forgetting here. Better than paying 40 bucks for a soldering iron in a tiny town somewhere.
 
I’ve done the two basses thing. Specifically to have a 4 string and a 5 string but at this point I decided just to learn everything on one. Until I’m playing with a bigger name artist who’s headlining (one can dream) I think just play on one unless the artist asks for something like that
 
I usually only bring one bass to a gig -- sometimes two, if I have to travel any distance to the gig. I get a tone I like and just ride that throughout the gig. And I have found that there is a lot of forgiveness in the mix -- if your tone isn't what you want it to be, sometimes it doesn't matter after you've started playing.

Having said that, I think having four basses on stage is a perfectly legitimate schtick. You can just make it part of your performance. My only two pieces of advice is that many of your stages are going to be small, so you need to be able to share the stage with your four basses, which means getting a stand/case for them that doesn't take up much room. And you need to be able to change them quickly. Playing four different basses at gigs can be an entertaining part of your act, if suddenly you're playing a different instrument. But if the change isn't sudden, if you're taking extra time between songs because changing your instrument is taking a long time, then it's not an entertaining part of the show any more. You have to be able to do it quickly.

If you can manage that, then have at it! It will be your thing, something not seen in other bands. And that's always a good thing, assuming you can pull it off efficiently.
 
I’m mostly a recording hobbyist, but a songwriter I respect asked me to play an extended set with him, and I jumped in. I’m having a great time woodshedding the material. Feeling some rare musical fulfillment.

First few times running through the material, I was on my go-to P with flats, but pretty quickly one tune started to beg for the fretless. So I got that locked in; sounds good.

And then another—90’s R&B vibe in A-flat—really wanted the 5-string with rounds. Done.

Last night, as I was packing up the 3 basses for today’s rehearsal, I thought “Am I insane?” I want to get the perfect sound for each song, but am I going to look ridiculous up there? Like I’m in an 18-song flex all about myself?

It was shortly after that thought that I decided to refresh myself on something real quick and, with the P packed up, I just grabbed the Mustang off the wall and…smh…now I need to have that sound (Mustang, La Bellas, foam mute) on this one song.

Is 4 basses over 18 songs a ridiculous look? Will I hate myself at the end of the night—or more specifically, will my 55-year-old back hate me? For you guys, what’s the most basses you would bring to a gig?

In the studio this would be totally acceptable and fairly normal. However in a live setting, especially when there are only 18 songs that’s completely overboard. One bass would be expected. Each bass will require a different EQ so every switch is going to throw a wrench in the mix.

Just go with the bass your most comfortable on or that sounds the best without adjusting EQ between songs.
 
Nobody will hear the difference when you swap basses, so you’re just creating extra hassle for the sound person. And at the gig, there’s basically one of everything else, and any one of those things might blow up your performance. You might as well bring just one bass and take your chances.
 
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Yep, one bass for me for a whole show. Unless I need something really different (like I switch to my guitarron or synth bass). As others have said, in the studio, have at it, go crazy. Producers love a guy coming in with interesting options (as long as one is a good pbass).
 
4 basses for 18 songs is way, way, way too many for me. I've learned the only person who is likely to care about the bass tone besides me is any other bass players in the crowd. Otherwise, folks just wanna hear/feel it, and I'd say nailing the material is far more important

This...

I bring 2. Main and backup. The ONLY time I didn't bring two (a one hour plug and play gig, band 3 of 4), the nut broke the first time i hit the D string (I string BEAD). Made it through the show but it was weird.

Never again....

(yes, I am tempted to say it. however ....)
 
When I gigged monthly, I’d bring 2 basses total. One as a backup. Usually one active and one passive. If one bass wasn’t sounding good for the room during sound check, I’d switch to the other bass. Or between sets.

I used a 5 string on some songs, though I could easily use a 4 string on them. One gig I started on my 4 string, switched to my 5 string 2 songs later, and then just stayed on the 5 the rest of the night. Switching back and forth is too much effort, and you don’t always have time between songs to do so.

And as much as it pains us to hear, most people in the audience won’t hear the different between your passive fretless with flats and an active 6 string.

Now for recordings, I definitely would choose the right bass for the song, but not live playing.

Oh, also my singer would like to call audibles 3 songs in to the set and just use the set list as a menu to pick from for each next song - so changing basses for a particular song wasn’t practical when the singer would kick you off on a song you weren’t expecting. (the babd would spend hours arguing the order of the set list, including the guitarists who had to switch instruments or pedal setups for certain songs, or even the drummer who might need to switch to brushes - hours spent negotiating set list order, and then everyone making notes on their set list for changes they needed to do between songs. Then the singer would say he wasn’t feeling it, or wanted a more high energy song early - which left slower songs to pile up later in the second set, one after another. It was a nightmare - but I seriously digress. We broke up for a reason! Hahaha.

Point being, sticking with one bass for the whole show just makes it easier and less stressful when unplanned changes are made.
 
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With the NewGrass band, one - Eminence Electric Upright, spare strings and bridge in case something goes awry. With my Americana band, the Eminence and a P bass with flats. About 60% of the songs on electric. I will note that I've seen some really top-tier players at recent concerts (Leland Sklar with Lyle Lovett) and he did a 2 hr show with one bass.
 
The only times I've found it reasonable is taking an upright and an electric. I've taken two electrics to a gig a couple of times and it was always an extra pain and not worth the effort. Unless you play really crazy stuff in wildly varying tunings or you very much need different acoustic/electric tones, I can't justify the hassle.