We just received a bid that drain tile in our basement will be around $9k.

Sounds like turn overs are a drain on you, but a good source of income for your property manager.

Barring any weather or drain  damage, properly sized duct work will out last us all.

A furnace or water heater going out is a pretty quick drain on cash reserves.

We are at the top and you can probably put that money to use somewhere else.In my situation the HOA was sued by an investor for $150,000 and it totally drained the HOA reserves. 

Luckily, we knew a plumber and were able to install a sump pump system that drained out to the alley (a ton of hard work - digging a 3 ft deep trench 50 yards in the classic baltimore rocky soil).

An electric water heater does not require any special maintenance (only drain) once per year (any handyman can do it).

Verify water drains quickly.

A while back I thought something had died in the vents - but it turned out to just be a dirty condensate drain which was breeding mildew or whatever.

He says we did it right and can't see any blockage of interior or exterior footer drains to sump pump that could cause seeping.