As a general rule the broken window principle applies to collections. In my condo some delinquencies have been allowed to accumulate for years, and now they discover that there is a one year cap on recovery under foreclosure. New board still under builder transition.
I have my bank autopay my fees a full month cycle ahead of due date including some extra wiggle room, to avoid the risk of a fee. If you can’t manage the cash flow risk of an income interruption, you might be over leveraged.
Unless there is criminal fraud, I choose to ignore the eccentricities of HOA presidents and board members who are volunteering their time to manage issues on my behalf for no charge.
They generally get paid with ego trips rather than money. I go out of my way to kiss butt and acquire goodwill, which you need if something comes up with your unit, or you wish to get away with bending a rule.
Special Assessment risk will be dependent on the quality of your reserve study and condo reserve policy, state regulations, what is depreciating. You may need to set aside some money for this.
Setting aside the lovenest aspect, you could list the property at breakeven and wait as a middle path.
Condos are always trouble. Wife will never own one again after we sell.