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What is the most expensive string you've ever bought?

Bass guitar strings are cheap. The Thomastiks I use on upright run around $300 a set, 2 basses, yearly string change. I could go nuts and spend about $900 on a set of Pirastro Eudoxas, but that's not practical or necessary for my gigs. My Serek's Thomastik Jazz Flats are at least 5 years old and still sound fine. I don't anticipate replacing them before my playing days are done.
 
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The most expensive set of strings I ever bought are the La Bella Deep Talkin’ Bass Gold Flats (5 string set). The 5 string set costs $61.50 after taxes. I didn't like them because the gold luster came off quickly, they made my hands stink, and they were way too tubby.

Tied for second are the La Bella tapewound series (regular White, Gold White, and Black) and the Rotosound 55 pressurewounds. Each 4 string set costs $52 after taxes. None of them gave me the sound I was looking for after experimenting with them over the last few years.

Thank goodness I switched to D'Addario nickel rounds this year! And thank goodness for my bass tech who put them on my Rickenbacker 4003! Each 4 string set costs about $25 after taxes, which are the least expensive strings I have bought in a long time. Me, my basses, and my bank accounts are better off after switching!
 
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I tried Thomastik and Optima. The most expensive part was finding that neither was for me (except maybe I could use the TI flats for the "thump" effect).
Next to that, Rotosound 77 and 99. The 77 was the worst built and most inconsistent string I've ever seen, yet it sounded great esp. the low 2 strings. The 99 was great in every way, except taking slightly longer time to install.
 
TI Jazz Rounds JR344. (~$80).

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Would have to be one of my six string sets for my Ibanez. Used to regularly buy d’Addario stainless steels or nickle-plated; seems like they sold for around $35 to $45 a pack. Switched to Rotosounds Swingbass 666s when d’Addario discontinued the Prisms. I believe they go for around the same price.

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Great strings; miss them a lot.
 
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I'm not sure which exact set of strings was the most expensive I've ever purchased but there is a segment of what I would call "hi-end" strings with much higher prices than "normal" strings. The ones I've tried in this hi-end segment are Thomastik Jazz Rounds Thomastik Jazz Flats and Dogal R44 Vintage Flats. I guess Optima Chromes and Optima RBs also belong to this category of hi-end strings. These are just the ones I have personal experience with.

These are nearly all "niche" strings that may not be a good match for every bass player or every style of music but they are all superb quality strings that (in my opinion) are in a completely different league to most "standard" strings out there.

All of these manufacturers also sell less expensive "standard" roundwounds btw.

However, this doesn't mean that the strings I've listed above are my absolute favorites. Like I said, they're niche strings that I reach for when I need a certain tone/vibe. My allround favorite roundwounds are probably the reasonably priced Roto 66 steels. My favorite short scale flats will always be Pyramid Gold (but I guess these are close to the "hi-end" category, at least based on current prices!).

But the objective quality of the TIs, Dogals and Optimas listed above is head and shoulders above most "standard" strings IMO. They will last forever and have an absolutely wonderful tone when you need THAT specific tone. That doesn't means they will be the best choice for all players, all of the time.

I also think there are some strings that have a "hi-end" price without really feeling like "hi-end" strings. Dunlop flats is an example of this. Don't get me wrong, they're great strings. But there's nothing really unique about them IMO. I could get reasonably close to that tone with a set of Fender 9050s at a fraction of the price. But with strings like the TIs and Dogals mentioned above there really is no alternative, if you want that specific, unique tone/feel.
 
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DB strings are much more expensive than BG strings. I’ve been paying over $100 a set for decades. For a while I used Velvet Garbos which were over $300 a set and are no longer made.

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One popular gut string set for DB, the Pirastro Oliv is almost $900 a set.

The most expensive BG strings I’ve ever bought ar the Ernie Ball “Group” strings. I’ve used Group II (medium) but have switched to Group IV (light). Currently $40 a set.

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