As for old records vs. new … just go for it! There are no rules. Some remasters sound better than the originals, some do not. The sport is in the listening. I have thousands of LP’s, some sixty-year-old originals (the first record I ever bought brand new is now 58 years old!), some remasters and some new releases. If have not found the sound quality of these to be a function of their age, but rather of their pedigree.
There is one category in which vinyl has a monopoly, direct-to-disc. The best of these are simply stupendous and cannot be equaled by any digital means. Look for titles from M&K, Sheffield Lab and Chasing The Dragon.
As for remasters, I must give homage to one man who should be canonized for his amazing contributions to lovers of music, Chad Kassem. He has been remastering albums of many genres with an attention to detail and commitment to quality that in most cases surpasses the original by a wide margin. I have many hundred of his remasters, mostly on the Classic Records and Analogue Productions labels. The worst of them is fully equal to its original and most are far better. Do yourself a favor and buy them all (I’m still working on it!) Or buy them from him in person at AXPONA (he is Acoustic Sounds) in April and tell him Dave sent you.
Another source of inspiration, who should be canonized as well, is Michael Fremer. Check out his blog Analog Planet, sponsored by Stereophile magazine, for inspiring reviews of both technology and recordings