A boiler that fails in January on a 12-unit costs more than the whole summer's reserve if you haven't touched it since March.
The number that gets first-time owners is not the repair itself but the cascading liability: in most states a heat failure that lasts beyond 24 hours gives tenants the right to withhold rent, arrange their own heat and bill you, or terminate their lease, depending on local code. A $400 boiler tune-up in October sits against that exposure and it isn't close. Get a licensed HVAC tech to service the boiler or furnace system before the first cold snap, not after, and get the service record in writing because you will need it if a tenant files a habitability complaint.
The second thing that surprises people managing five or more units for the first time is how much a single pipe failure touches. One frozen supply line in an exterior wall can affect four or five units simultaneously, and the water damage runs well ahead of the plumbing repair. Any pipe in an unheated space, crawlspace, or exterior chase needs insulation wrap before November. Walk the basement and utility spaces yourself with a flashlight, because a property manager who charges per-incident will find the problem after it costs you.
Weatherstripping and door sweeps across all common areas and unit entries are not glamorous but they show up directly in the gas or oil bill. On a 12-unit where the owner carries heat, a 15 percent reduction in heating loss across 12 doors and a lobby is real money across a five-month season.
The reserve question matters here too. A single boiler replacement on a building of this size runs $8,000 to $18,000 installed depending on system type, and most first-year owners have not budgeted for it because the inspection said "functional." Functional in May and functional in February are different standards.
What does your current boiler or HVAC system look like, and do you know the install year?