Budgeting with reserves: Roof, HVAC, and everything else that will wear out over time.Home warranty buyers = people bad at math. 

The cash on cash return is through the roof.

I wouldn't worry as much about the age as I would what it would cost, how much it would rent for, how well it is built and when major repairs will be needed (ie how long will the roof last).Also for the two-are they both condos (ie strata/condo fees) or is one freehold and the other a condo (ie one has condo fees and the other doesn't)? 

Correction coming, already started. insurance through the roof.

Multiple improvements done on this duplex in 2021, including new roof, gutters, flooring, drywall, electrical, appliances, and heating/cooling unit for the second floor.

If have RCv vs ACV all that means is a 90%+ discounted roof replacement every 17yrs on average.

Structural, roof, mechanicals, cosmetic? 

It recently had some roof and ceiling damage and we are looking to sell.  

Roof and HVAC are in good condition.

However, given a lax board and the community's preference to avoid assessments and projects I believe no major repair or replacement work has been done since the building was built in the mid 80's (i.e. roof, plumbing etc.,).