Current levy amount, sinking fund balance, last 10-year forecast, recent and pending special levies, insurance coverage and excesses, by-laws (especially pets and renovations), minutes of the last 2 years of meetings, and any active legal disputes.
Red flags: a sinking fund balance under $10,000 in a 30+ lot building, repeated special levies, ongoing defect disputes, building insurer changing every year, lots of repeated complaints in the minutes, manager turnover. Green flags: rising sinking fund, regular maintenance program, calm and well-run meetings.
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