"Investment" is tricky. I've also been down this road, albeit almost exclusively with used basses, so as not to take the depreciation hit if things don't work out. I now have a main player that I bought new (a Carl Pedigo build, per my avatar), but I probably went through 50 basses over 10 years, during which I learned what I needed to in order to know what works best for me. This included sorting out whether to play 4 or 5 string, and once down the 5-string rabbit hole, preferences in ergonomics (body shape, neck shape and width), string spacing (I've learned I'm a 19mm kind of guy), scale length (I can do 35" but usually prefer the sound and feel of a 34" G string), fingerboard (rosewood on my main player for pragmatism in folklorical and and rock contexts, but I'll always love ebony when centered pitch and a quick attack, as in a soloistic jazz situation, are key) and body wood (love alder, really love mahogany, but have ended up as a light ash kind of guy - who knew), number of frets (have found 22 to be my sweet spot, although I miss those last two for soloing), type of frets (vintage is my jam), electronics (not a J-type guy), and hardware (tuners and bridges can make a big difference in operational ease, and bridges certainly affect tone). My Pedigo reflects the sum total of a lot of thinking and learning about what works best for me.
But of all of these incremental steps, the single most important was when I took the plunge from mid-priced basses to a used Sadowsky Metro 5-24. It was a huge revelation in the way of tonal flexibility, clarity (superb B-string), playability and overall quality, and I realized that good boutique instruments really are superior tools. I went through 5-6 different Sadowskys, one new, the others used, all in a range of styles, and realized that for me the 5-24 was the best of them, although I'd love to live with a Will Lee 5 with soapbars at some point, which comes closer to my Pedigo build.
So on a few instruments I lost money. On most, I broke even. On a select few that I was able to buy for a song, I made some money, but nothing dramatic. Meanwhile, I learned a huge amount about the range of voices available, and the importance of ergonomics in being able to realize the sound that you want as you find a bass that fits you rather than fights you. I now have a small group of keepers that I would not have been able to identify without all of that trial and error, and I know a whole lot more about basses and their construction than I did at the beginning of this exercise. So on a money basis this experience, including shipping costs, probably reflects a modest loss, but on a knowledge basis, it's been hugely successful, and I would not have my "keepers" without going through this cycle.
My priorities and choices are necessarily subjective, but one thing that is objective and undeniable - any Sadowsky is an extremely well-built instrument that reflects a "constant quality improvement" orientation, and is a superb tool. I've heard some folks question certain Fodera design choices from a mechanical view, but based on what I've heard from the sound of these axes, and a short custodianship of one, the Foderas are also excellent tools and the cost is justifiable if you are chasing those sounds.
Last observation - it does not look like enough folks have been exposed to the Sadowsky 5-24, which is capable of some Fenderish tones, particularly with the neck pickup strongly favored, but otherwise is very much it's own beast, with a superb B-string. Arguably the 5-24 and Modulus Q5 set a standard for uniform timbre from low B to high G, and for high-fret usability of the B-string, that is in a class of its own. Which, of course, introduces the question of whether there are other builders in the Sadowsky and Fodera class - there are, but very few that can match Sadowsky and Fodera for ultimate quality and utility, demonstrable over a long history of high-end professional use.
EDIT -- Alembic. Been there from the beginning, and still doing it. To paraphrase Richard Thompson: "Now Nordys and Mike Lulls and Allevas won't do - they haven't got the soul of an Alembic '72…" And Tobias/MTD. Mike Tobias and Alembic both have the product and track record to be in the same league as Fodera and Sadowsky. Yeah, I guess Stuart Spector and Ken Smith as well. Clearly a group that has experience and longevity going for it…other, younger makers may also be in this league for quality, but the classics are classics for a reason - they are great, and they have stood the test of time.
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