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What 5-String Should I Try?

Another oddball suggestion, but maybe a Dingwall Combustion (it's in the upper part of your price range). The fanned fret system is really incredible and it is stupid easy to adapt to. The low B is amazing, as are the necks and tension. The tone is jazz bass-ish, active/passive and mine is my new go-to.

I like the Dingwall basses too. If I win the lottery, I'm getting a Canadian built one.
 
Can't speak to the Sire. Also consider the 35" scale question, which applies to the Lakland 5-stringers.

For around $1500, and if you prefer passive, I'd suggest trying to find one of the Fender Roscoe Beck V basses. Superb tonal flexibility and cojones for a passive bass, and really well built (as good as Fender custom shop). Main downside is a bridge that is PITA to adjust because it is too darned adjustable, but these are great basses, and used they go out in the $1300-1600 range, so you should have little trouble getting your $$ back if you have to flip it. (You'll only find used as these are long discontinued). If you come to need active, go get a Sadowsky stomp box and groove accordingly.

Disclosure - I have a Roscoe Beck IV, and love it. I've also owned the 5, and would still have it but for finding something with better ergonomics, for me.

And the EBMM SR5HH is also a very serious bass, if you can get with the narrower string spacing. If you have an SR already, I would not bother with the single-pickup option.
 
The EBMM SR5 and Sterling 5 are different enough from the Stingray 4 that I would give them some serious thought. They can get a similar sound to what you're used to, but with the 3-way switch and a little EQ, they can do a lot more, IMO. I'm less a fan of the HH/HS versions of those, but those are very nice, too.

Another serious contender, and one of my personal favorites, is the EBMM Bongo 5. I have an HH, but I wouldn't mind an HS. Or better (for me), a fretless HS w/Piezo. Sure, they can do a "Stingray-esque" vibe, but they definitely don't stop there (or even start there, really). Very versatile, and far warmer than I first imagined it would be before I tried one. With everything flat, it sounds warm and clear - very supportive, and a great fit in rock/pop/country/blues scenarios. The 4-band EQ can do just about anything, though. I often get a pretty close "Pbass" approximation with the front pickup and some EQ adjustments. Close enough for rock'n roll, anyway. If I need closer, I pull out my Pbass. Of course, if you're after a Jazz bass, the Bongo isn't gonna do it, but it's very usable bass with an excellent feel and nearly perfect balance and great tone, with a B-string as good as anything out there.

Right behind, or maybe parallel to the Bongo, is a G&L L2500 with the "K-switch" option (single coils). That is an altogether different animal, but fabulous quality, fit, finish, and TONE. G&L also offers the M2500, with slightly more modern pickups and a more conventional 3band EQ. Since you're also interested in a Jazz 5, they have the MJ5, which is basically the same bass as the M2500 with a Jazz-style pickup. Not single coil, but a linear 'bucker like Sadowsky and others use.
 
I play a ebmm stingray so I say that, or a lakland 55-01 or 02, warwick corvette standards you can find used for 700-1200 bucks, and ibanez btb basses are fantastic, and of course theres dingwall
I have a Stingray 4H, but I want something different for my 5-string. I love the Stingray sound for rock and anything more aggressive, but I haven't liked it much for jazz, "church music", weddings, trio groups, etc....it just seems like it wants to punch everyone in the face all the time, which is great for some stuff, but not for the settings I find myself in these days.
 
Another oddball suggestion, but maybe a Dingwall Combustion (it's in the upper part of your price range). The fanned fret system is really incredible and it is stupid easy to adapt to. The low B is amazing, as are the necks and tension. The tone is jazz bass-ish, active/passive and mine is my new go-to.
I really want to try a Dingwall sometime. I don't think I've ever seen one in Oklahoma, haha!
 
The DJ5 has a cool factor that I can't get over. I can't explain it.
I hear ya on that – no need to explain. It is a gorgeous looking instrument. But as Joebone inferred above, considering your current herd is all 34" scale, the DJ5's 35" scale might or might not be a consideration in your choice. If at all possible, play before you pay.

In the 34" camp, the Yamaha BB series has some nice 5-string P/J options. In the 35" camp, the MTD Kingston Heir is a terrific instrument. Both are within your budget purchased new.
 
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For my first five string I'd stick with a 34" scale. Then if you were to buy another I'd look at 35". I'd try to find a Stingray 5 that was my first five string and I played it for a many years before they had the HH option. I have not tried the Marcus Miller Sire but I have heard good things about them.
 
I hear ya on that – no need to explain. It is a gorgeous looking instrument. But as Joebone inferred above, considering your current herd is all 34" scale, the DJ5's 35" scale might or might not be a consideration in your choice. If at all possible, play before you pay.

In the 34" camp, the Yamaha BB series has some nice 5-string P/J options. In the 35" camp, the MTD Kingston Heir is a terrific instrument. Both are within your budget purchased new.
What impact does the scale have? Does it create longer distance between frets?
 
Can't speak to the Sire. Also consider the 35" scale question, which applies to the Lakland 5-stringers.

For around $1500, and if you prefer passive, I'd suggest trying to find one of the Fender Roscoe Beck V basses. Superb tonal flexibility and cojones for a passive bass, and really well built (as good as Fender custom shop). Main downside is a bridge that is PITA to adjust because it is too darned adjustable, but these are great basses, and used they go out in the $1300-1600 range, so you should have little trouble getting your $$ back if you have to flip it. (You'll only find used as these are long discontinued). If you come to need active, go get a Sadowsky stomp box and groove accordingly.

Disclosure - I have a Roscoe Beck IV, and love it. I've also owned the 5, and would still have it but for finding something with better ergonomics, for me.

And the EBMM SR5HH is also a very serious bass, if you can get with the narrower string spacing. If you have an SR already, I would not bother with the single-pickup option.
That Roscoe Beck has my interest. Where are these things found for sale, though?