I'm with dioxide45 and others in his camp on this one. As an example, if an owner had just purchased a resale week here a year ago, and now has this special assessment hitting to make up for prior owners essentially underpaying for this maintenance that surely should have been known about and planned for, that new owner would surely be justified in being more than a bit upset. This is the very reason there IS a reserve that gets paid into in the first place.
Specifically from the HOA
It is always the Board's intention to adhere to its fiduciary responsibility of managing the ownership's money carefully and curtailing increases to the annual maintenance fee, while at the same time maintaining owners' expectations of the resort. In order to do so, the Board was forced to choose between a substantial one-time 'special Assessment" in 2018 or an increase in the reserve fee by a fixed amount over a four-year period, in order to fund the upcoming work. 'We chose the latter to be a more acceptable approach
Now back on point. I do not have that crystal ball that gives advance warning of what will go, when it will and how much it will cost. I do not expect my HOA to have one. If something big goes before it is suppose to and it costs a lot of money, you have a short fall.
As far as a recent owner having to foot the bill on underfunding is no more an issue than a the person who sold to an over funded situation. I do know someone who purchased at the Monarch two years ago that did so at a price of 50% less than I did my resale 20 years ago. My resale 20 years ago was purchased 50% less than new. In the 33 years the Monarch is open they has 1100 of special assessments including the total of the last one. All of it has been in my 20 years of ownership. I have no problem with that. I do not feel the least bit sympathetic to the person who purchased two years ago and neither should anyone else. They got a steal even with the assessment. BTW, the person was me.
An SA may or may not be the fault of the HOA. Every situation is different. I am sure that there are situations where an assessment should have been avoided. The owners get to decide that, not me as an outside looking in.
I just purchased an EOY 2 BR at the Grand Chateau. I did look at the increases the last few years along with details of the reserve fund and the useful life of the items in it along with were the items are in the useful life. I looked to see if the builder was supplementing the MF. I tired to do my due diligence because like diamonds, MF's are forever. I paid under 1800 and if there is an assessment, I can understand many people being upset if it was underserved. Paying 1800 I did not earn the right to be one of them.