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New Bass Player Seeking String Advice

Blues, classic rock, and maybe a little country (older stuff, not modern country).

You want warm tones. Flats are the traditional choice. Pressure wounds may also get you there. I don't have experience with pure nickel, but I've heard they are on the darker side, too.
 
Blues, classic rock, and maybe a little country (older stuff, not modern country).

That's mostly what I like to play, too. Most of the basses I use for that have flats (La Bellas & Rotos); for late '60s stuff, some have nickel rounds (my Rickenbackers). For the stuff that was originally done with an upright, I've been using a violin bass with Roto 88 tapewounds. Nothing electric and fretted will sound exactly the same, but this is as close as I've come so far.
 
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I want to comment beginning with your name, "Entwistle Fan". I, too am I diehard Entwistle fan, and being that shaped my long journey of trying different strings for many years (been playing since 1979). I usually tried to use Rotosound, since JE basically invented them, and I was satisfied, but I could not afford to buy new strings very often. I tried lots of other brands of roundwounds, and to me, for roundwound strings, a new set sounds like a new set no matter what the brand. I also have learned to love flats in my old age :). Especially on my Danelectro. I hate finger noise, so they are nice about that. I am currently trying different flatwounds and groundwounds and comressionwounds, and I have been pleased with D'addario, GHS, and LaBella. I am going to check out GHS pressurewounds next. If I win the lottery I might try Thomastik-Infeld.
 
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My recommendations as a starting point for most people is DR Sunbeams for roundwound, and D'Addario Chromes for flats. Sunbeams are warm but have great grind if you want it, Chromes are a great intro to flatwounds; kinda like roundwounds but with the smooth feeling and big fundamental of flats.
 
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Chromes can also be a misguiding first flatwound string, IMO, in that they are very bright sounding flats for quite some time before they mellow out. A bass player who is used to roundwounds might give up on them before they are fully broken in, and conclude that flats aren't worthwhile.

I would rather recommend a darker sounding string to a "flats virgin", like GHS Precision, LaBella DTB or Sadowsky.

The best reason I can give for testing Chromes is their price and availability, again, my 2 cents.

To the OP: I play blues, classic rock and old school country as well, and I have flats on both my basses: TI JF344 on a Fender P '59 CS, and Sadowsky SBF45 on a Fender MIJ 51 P bass.
 
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Chromes can also be a misguiding first flatwound string, IMO, in that they are very bright sounding flats for quite some time before they mellow out. A bass player who is used to roundwounds might give up on them before they are fully broken in, and conclude that flats aren't worthwhile.

I would rather recommend a darker sounding string to a "flats virgin", like GHS Precision, LaBella DTB or Sadowsky.

The best reason I can give for testing Chromes is their price and availability, again, my 2 cents.

To the OP: I play blues, classic rock and old school country as well, and I have flats on both my basses: TI JF344 on a Fender P '59 CS, and Sadowsky SBF45 on a Fender MIJ 51 P bass.

Well, I think it's two sides of the same coin; if a guy has only eaten white chocolate and wants a change, do you recommend milk chocolate or tell him to go straight to the 90% cacao stuff? Similarly, do you recommend the most roundwound-like set of flats so it's got the flats vibe but not so far from the roundwound sound that you don't need to change your setup, or go the whole hog and get the most typical sounding and feeling flats but may have a lot of tweaking to do? GHS Precisions were definitely my second recommendation so I'm with you there.
 
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As for sound, I am playing acoustically the majority of the time with only about 25% of my playing being plugged in. Regardless, I think I am still too new to have any clue with regards to sound/tone (and is tone even something I should be worrying about just yet?). I like the sounds I am getting as I learn but more experienced players might think my tone sounds like crap.
I encourage you to avoid thinking about what other players think at this point (or ever, really). Figure out what you like -- if you're excited/motivated by what you hear when you play, you'll just play better. That said, it's a good idea to play amplified while trying to figure out what strings you want since you simply can't make an informed decision about sound when playing an electric instrument unamplified.
 
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Well, I think it's two sides of the same coin; if a guy has only eaten white chocolate and wants a change, do you recommend milk chocolate or tell him to go straight to the 90% cacao stuff? Similarly, do you recommend the most roundwound-like set of flats so it's got the flats vibe but not so far from the roundwound sound that you don't need to change your setup, or go the whole hog and get the most typical sounding and feeling flats but may have a lot of tweaking to do? GHS Precisions were definitely my second recommendation so I'm with you there.

That is a fair point. I guess it's down to expectations, if the OP expects a change in sound and/or tension, maybe Chromes could be misguiding. Definately could be thought of as positive that you don't have to do a complete setup, although I think everyone should learn to do their own setup too.