I think you've going through the right factors. Quality of Condo Board is always tops on my list. A good board making the right decisions is the key to *everything*.
Reserve fund is next - scrutinize the boiler and elevators hard - most special assessment are for this, barring gross builders negligence for mold like you find in some new builds. Have they got enough?
After that - what's your end game? To hold till you die as an income generator? To sell when it hits a certain price? To move parents into eventually? Have a goal in mind it'll make your decision that much easier.
If it involves renting for a while - it becomes a business decision - look at it that way. Is it easy to rent out? Is it attracting low maintenance tenants? Is it worth upgrading to try and attract a better class (and higher rent) of tenants? Is it in a desirable area with capital upside in your time horizon?
More importantly are there any dark clouds on the horizon to all of the above?
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