I'm in a small complex, and hindsight is 20/20.
- Savings philosophy - how are contributions to reserves made, how often, what have reserves been used for in the past? (This will get at whether there is a savings plan, or whether savings are just a happy afterthought. Also, some owners may want to tap reserves for any unanticipated expenses, and some will want to save for infrastructure issues.)
- History of special assessments (This may be a better sign of how they handle those than upcoming assessments, especially if they don't tend to plan ahead.)
- Decision-making process (Do they have frequent meetings? long email chains? All members involved or just the Board? For ex., our Board handles most issues. Most of the other owners don't want to be bothered, but one gets irritated about not being consulted. You also want to find out if they can make decisions, or if things slip through the cracks a lot.)
- Infrastructure maintenance plans (Do they have one?)
- Is there a professional property manager, and what is their role?
- How are Board positions rotated, or are they? Who handles day-to-day maintenance, finances, etc.? (There's not going to be much rotation in a 5-person HOA, but has one person has been handling all the finances or all the maintenance for 5+ years?)