There's so much good stuff out there for a buck or two per Lp. I usually just recommend collecting London Stereo Treasury orange label Lps (not the US domestic yellow labels).
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There are some good Reader's Digest collections. Shoot for stereo. Some of my favorite collections include "Festival of Light Classics," "Music of the World's Great Composers," and "Treasury of Great Music." Most of the recordings used very good conductors and pick-up musicians from the London Symphony Orchestra. All of the recordings were made by RCA and sound like it. Some of the pieces have rather uninspired performances, but almost all of the recordings are good.
The Reader's Digest box collection of Rachmaninoff Piano Concertos is rare, but well worth it even of you can only get it in a mono recording set. Some of the best ever performances of Rachi's work.
As an additional note to Bpoletti's post, I have found that when buying used vinyl, sets offer a combo of both great value and good condition. YMMV, of course, but in my experience, most of the sets I've bought are in better shape than the single LPs. Perhaps their owners cared more about preserving their purchase, or they just were too bothersome to pull out of the box, but they are rarely beaten up.
Don't forget to look for local record shows, shops and yard & estate sales where you can visually inspect the records before you buy.
Yes, I've found quite a few good classical for a buck or two. But if you want demo quality to show off a system, then the ones I mentioned above should be top of the list. I usually buy the new remastered version from places such as acoustic sounds, music direct, etc.
Expect to pay good money for these titles as there're all sold out and difficult to find, Lieutenant Kijie is still available I believe. An alternative to Moussorgsky Pictures At An Exhibition Fritz Reiner is Power of the Orchestra on 45rpm which I'm sure is still available for 50 bucks.
You want a strategy? Start with Beethoven. You'll hear the evolution of late classical to early romantic through his 9 symphonies, and then you can go to Brahms, Dvorak, Bruckner, Mahler, and on through the 20th Century. You can always go back to Bach. :) And if you don't like something, listen to it again.
you can go to Brahms, Dvorak, Bruckner, Mahler
Good suggestion to start with Beethoven - try his Emperor piano concerto and symphony #6 (pastoral)for starters.
And don't forget Tchaikovsky, Wagner and Sibelius !
The OP lists some sonically outstanding recordings from Fritz Reiner and the Chicagoans - to that group you can add Also Sprach Zarathustra by Richard Strauss.
Like anything else, classical music is a matter of preference. For example, I tend to gravitate towards the Russian composers. Others may prefer German/Austrian composers of a particular era. By buying large numbers of classical LPs from various composers at cheap, record show prices, I have been able to listen to a lot of music and refine my taste with a minimum outlay of cash.
I've mentioned this before a while ago but thought I'd do so again. I would strongly recommend classical music newbies go to the Naxos website and invest in a one year ($20) subscription to their on-line catalog. You will be able to listen to over 5000 full length recordings in good quality sound. You can explore to your hearts content at your convenience. I think it's a cost effective way to have pretty much the core classical canon at your fingertips.
Sibelius brings up an interesting point. Is this newbie a vinyl person or digital? Young or not? I think people who are new to classical music are less likely to put up with bad sound or OK sound, unlike pop or rock. CD was my intro to classical music, and still offers great sound, while vinyl is a very different experience. Labels like Naxos offer reliable, often excellent sound and often great performances for cheap. I'm listening to classical music now on used records, and the sound quality is variable, and I would have been less likely to put up with this if I was a newbie.
It's also interesting that none of the major classical labels are making vinyl pressings anymore, unlike pop or rock.