Quality: vinyl then versus vinyl now...

What is the difference? If I buy a 1.99, NM copy of somethng and say Music Direct has a new pressing of it for 39.99, is it that much better? Maybe some? None at all? I seem to be finding a wide difference for used NM or Mint copies of vinyl as compared to new pressings that are high enough to break the bank.
depends on the label..then and now..remember,todays vinyl runs are quite small and facilities are few, and since pressing an lp is much more expensive than a cd or sacd, some companies' investment(particularly after remastering) can eat up most of the profits..add the artists royalty and there you have it..a $30 lp. in general though, original pressings from the 50's and 60's are better,seventies and 80's are worse....although there are lots of exceptions.
For original recordings from the past, the closer to the master tape the pressing is, the better the sound generally is. This is more important than the quality of the vinyl pressing itself.

Therefore you should seek out the earliest pressing from the country where the record was recorded and mastered if possible. UK '60s Beatles pressings, US Blue Notes, etcetera.

Most LP's nowadays are not necessarily any better...just on heavier vinyl and quieter. I've been very disappointed in most companies pressing LP's today, spending more than $20.00 a pop, and being very disappointed in the sound quality. Many people seem to think it's that the master tapes are no longer in good shape, but I believe it's poor quality in making the vinyl masters. Classic, Sundazed, Cisco and DCC seem to do the best job.

If you are selective and can find little-used copies, you will probably find a lot of bargains in older vinyl. RCA Living Stereo & Victrola from 1958-1962, Decca UK or London from late 50's to the early 70's or Lyrita for classical will give some incredible recordings. For popular music, Island, London, Decca, MCA, Warner Bros., A & M can provide some classic recordings. There are many more labels and a lot of exceptions, even on labels that are usually not that dependable.

UK and Holland pressings are pretty consistent in the quality of recording and most often better than US pressings. I have been purchasing Japanese pressing for over 20 years, and although I have run across a rare bad example, there is an incredibly high level of quality. I don't know how they do it, but I often think that the consistent methods used in the industry in Japan allowed them to make better LP's than other companies even when they had less than perfect master tapes.
The records "then" were at mass production and so worthed less than nowdays that are custom built
The assumption on quality levels on both cases could be made quite logically...
There are $30 new ones which you can only find at $200 used. If you get a playable $1.99, of which I have hundreds, then the new ones are usually suprefluous, unless you are really into such comparisons of what is done with master tapes in different studios.
I wouldn't break the bank on re-issues w/out specific knowledge of an improvement. God knows from were Music Direct, etc. obtain their source material on a per album basis. Sometimes good, sometimes less good. Some labels have a reputation of better, more consistent re-issue LPs.

"Most LP's nowadays are not necessarily any better...just on heavier vinyl and quieter."

That's been my experience, with the Doors in particular. Good point, and for me sometimes worth the extra $$.