The condo market has really been hit hard by the downturn in recent years. This is especially true of Naples condos. As the Naples Real Estate market started to unwind there was an onslaught of new foreclosures. This was very scary to buyers because they were unsure if the HOAs could actually survive the period of non-payments. This is a reasonable concern; however, generally the associations eventually get their money.
When a condo gets foreclosed on the HOA holds a lien against the property as well. The new owner, the bank, must make good with the HOA before they can sell to a new owner. They are legally obligated for only some portion of it (I believe this is 6 months) but usually do not try to litigate the matter. Instead, the bank gives what is past due. So, while there were some periods where there was a high rate of delinquency, eventually the HOA gets their funds.