Table,cartridge,phono...where to put most of my money?

Stick with your digital set-up. Obviously there is something about the sound of an analog front end that you don't like. Have you ever heard one that you DID enjoy? If so, there must be something amiss in your set-up - maybe your phono stage? I would really like to know the specific areas that you found disappointing. 

If you’re not properly cleaning your records you’re just throwing good money after bad. Spend the 3K or so on a Degritter and you’ll see a bigger improvement than 3K could make anywhere else in your vinyl system. If you’re happy with the results, you have 3K left to allocate to updating the cartridge, amp and or TT. If not, you can probably recoup 75-80% of what you spent on the Degritter by selling it. Oh, and buy some good sleeves, MoFi or Diskeeper.

I have a vacuum cleaning system,left over from last time I did this venture 

I would keep the VPI.  Great Table.  Record clamp seems to deaden the sound.  Try a better Phono preamp.  Keep a clean stylus. Do not expect the same dynamics as digital.  Analog is a smoother sound.

@missioncoonery If you want to get the best fidelity vinyl can offer, you'll need to put more effort into it than digital.  With digital it's:  insert a CD, press a button and enjoy.  With streaming it's:  surf for whatever selection you want, press a button and enjoy.  Digital is unquestionably less work and the more convenient format.  However, with respect to comparative fidelity, my personal preference is for vinyl, provided it's done right.  The "is digital fidelity better than vinyl" debate is fast becoming the new or next "are expensive speaker cables really worth the money" trolling meme.  Some prefer and/or swear by digital and some by vinyl and that's perfectly alright.  To each, his own.  However, when comparing apples to apples, oranges to oranges (i.e.  quality components & source(s) of the digital to the vinyl sources), my ears prefer vinyl.  That being said, there are a host of factors that come into play in order to make a fair comparison, not the least of which is the condition of the records (e.g.  quality of recordings & pressings; cleanliness of records; dust mitigation rituals like keeping the stylus clean, brushing or blowing dust off records before play, etc.).

I have no idea what kind of shape your records are in.  However, judging from your reported experiences with your Linn and VPI turntables, assuming these were purchased new (i.e.  not used or otherwise defective in some way, including the cartridges) and set-up properly and also assuming there were no issues with the phono stage(s) employed, my initial suspicion points to the condition of your records.  This is why I tend to agree with those who've suggested by starting with clean records.  There are a host of ways to approach this, depending upon how much work, time or money you want to put into it (e.g.  manual cleaning; vacuum machines; ultrasonic machines; combinations thereof; etc.).  If you're not into sweat equity, stick to digital.  On the other hand, if you are really serious about wanting to get the best out of a vinyl format, I think a bit of reading & research would be in order.  Here's a little something that I guarantee will not be an easy read but, if you truly are serious about this, will be worth your time:

PACVR-3rd-Edition (thevinylpress.com)