Thank you for this inquiry on the never ending saga of liening of non-paying members versus going to court. We too have about 10+ years of owners with liens and costs.
If you research the owner on the Registry of Deeds, you will probably see that he/she has many other liens too. We have one guy who has federal, State tax liens and many other liens - except from municipalities. The Town can take your house, but all these other liens just pile up on the owner. According to one attorney, years ago, stated that when the house gets sold, the chances of our liens are less likely to be paid off due to the other liens.
Finally, a long time ago, at a MARA conference the paperwork was distributed to file it at a small claims court. I have not utilized the small claims court procedures. If the owner has a mortgage, I am aware that some banks will pay it off. In the past a MARA officer/member (Peter) shared his experience of going to a bank, handing them the lien, and they paid it off.
Clearly this owner you described has multiple properties and doesn't seem to be concerned about his/her neighbors. I find that when one owner has one property, lives year round in it is more likely to be interested in his/her membership within the community. We just had a 10 year lien just paid off. When an owner wants to refinance, they have to pay off their liens. Unfortunately, due to high interest rates, it is less likely people will want to refinance.