You sort of need a condo savings account that can be invested where the premiums you pay get invested. You need some laws or state regulations to make sure some minimums are maintained. The gains would then offset a potentially lower selling price since the HOA would have enough money to cover repairs.

But at the same time for a single family home, it is not unusual to invest 100k in a remodel if the location supports it on a 40 year old house. A condo should operate similarly although the scope of changes you can make is different obviously.