Look at the history of the HOA fees. Typically, after 37 years you are going to see an upward spiral in the fees which are completely separate from your PITI money. In other words, there will be items that prior board members didn't see as important - like new siding or new roofs or refinishing the pool, etc., and that were'nt budgeted for - and now deficiencies in the budget need to be accounted for - ie - higher HOA dues. Even though the unit might have the most updated interior in the entire community, the part that the HOA is responsible for (all of the common walls and their related parts like plumbing and electricity) could be extremely deficient. See what the HOA dues started out at and graph the difference between then and now. You might very well be better off spending that money on a single family dwelling unless it is worth it to you to pay into a fund so you don't have to do maintenance. Single family residence owners have the option to save for long term maintenance; condo owners do not.