Most months I don’t do anything and the money just flows in but when a tenant moves out I can usually expect to spend considerable time painting, upgrading, and showing.  

Based on the photos, I would opt for keeping the existing cabinets, making cosmetic upgrades and get a tenant in there asap.

Seems that in Western Canada at least (prairies), the numbers likely will not work if you are hiring a contractor to do all the work and are just "upgrading" and existing property.

Raised rents, landscaping, added fence and deck, major utility upgrades (water/sewer), converted sunroom from uninsulated/unfinished to true insulated 3-season room with new roof, adding updated fixtures and finishes, paint.

That doesnt count having to upgrade the disconnect which is potentially thousands more if you dont have the juice to handle a condenser.   

I purchased two properties (one for 50k and the other for 62k) that have roughly 30-40k in equity through upgrades and appreciation.

or Add more upgrades to further increase value?

The HOA fees cover any exterior costs like roofing so I only have to be prepared to cover issues inside the suite - although there usually are special levies every year that they charge a few hundred bucks for to upgrade/maintain various issues in the complex.

There will be a lot of repairs needed as they haven’t done any rehabs or upgrades since they’ve bought them about 7 years ago.

If possible please share costs this hvac upgrade may incur