Are we talking about new bands or older bands (with potential reissues?)
Bandcamp is a wonderful tool to explore if you have some patience and are willing to take risks. Most of those records are not "audiophile" quality, but neither are many of the reissues of old obscure bands-- though they are still worth listening to.
"Original" pressings (whatever that means to you, depending on country of origin, mastering, etc) of some of the old obscurities has gotten obscene-
This has forced me to finally confront and embrace digital in my main system for the first time (and, surprisingly, it doesn’t sound bad). The difficulty I have found is that the usual audiophile sources for high quality downloads don’t have a lot of the obscure stuff. So, it’s buying older CDs, some of which may have been taken from tape, and playing them via a CD transport or ripping them for a computer based audio system.
I have been on many vinyl binges over the years---but I’ve started to slow down with prices in the high 3 and low 4 figures for some of these records. (I’m not talking about a Tom Port type record, but stuff that is just costly because in addition to being obscure, it is often collectible). Although that market has softened for some records, the asking prices for so-called VG+ are nuts. And since most of these records don’t have a big market anyway, they are usually reissued, if at all, by smaller houses, often in Europe, from digital sources, which vary considerably in quality.
I’m glad I bought what I did when I did--not because of its financial value, but because it is unlikely that I could buy much of this stuff today at realistic prices, e.g. UK and German Vertigo Swirls, some of the early Italian and German prog and proto-metal, odd Japanese psych rock of the type covered by Julian Cope, the old Island pink labels, etc.
I listen to these records, and in some respects, I’m simply a caretaker for them. I clean them well and enjoy them. Tracking down the ’best sounding copy’ can be a frustrating and costly venture, even for an otherwise modestly priced old record, partly due to grading inflation and the cost of shipping from other countries.
Pure Pleasure has reissued a series of Strata-East label records that are a relative bargain; Speakers Corner did a great remaster of Herbie Hancock’s Crossings (an eclectic spiritual jazz/funk album). Some of the Polydors from the EU of bands like Blast Furnace are great b/c the sound is decent enough, given how difficult and costly it is to buy an original copy.
I would like to go to the Utrecht show at some point- I think the WFMU show in NY is one of the best record shows extant. I know people like the record show(s) here in Austin, but I find very little since I’m typically chasing non-US pressings and even among the US stuff, the rarities are often painfully overpriced. I guess if you get lucky, you’ll find some bargains in the bins-- I did a sweep of stores in Brooklyn a couple years ago and bought quite a few records without spending a fortune. But, it’s rare that I find what I’m looking for (on my ’list’); rather, it is taking advantage of what happens to be available and grabbing it.
One of my friends is constantly record shopping --even though he is a distributor and has a few small labels. Most of his ’finds’ are either dirt cheap obscurities or expensive obscurities that are priced well, compared to "market." It’s tough out there once you get beyond the standard reissue mill of audiophile warhorses.