Having 100 units under one roof gives you far more focus and economies of scale when it comes to maintenance etc.All your risk is concentrated on one pile.

New roof, solar, paint, lvp in the living room, granite countertops, cabinet handles, fixtures, carpet on stairs and upstairs, refurnished entire house.

If any of you could help me determine what kind of property damage I should avoid either because it costs too much to fix or it is just too difficult/ time consuming (things like termites, gas lines needing repair, roofing, etc.).

The  unit is rented consistently and is functional but also needs upgrades, new siding (has 2 layers), Some rooms could benefit from re-wiring and more insulation,   Painting is always an issue as it is not plaster but older thin wallboard. kitchen is fairly new, bathroom could use upgrade, upstairs bedrooms have some pitched ceilings but I don't think based on the foundation/construction it is a candidate for a full second story and it had a new roof a few years ago.

No... we replaced the roof, why put in a crappy hvac?)

Ins is through the roof as well. 

There will be a lot of no's but there are still ways to get them talking (it's in scripts - "Not even for $$$", I'm not calling to lowball you or waste your time", "I'm really just planning for my next one in the next 3-6 months"Get to the details like Capex - age of roof, furnaces, water heaters, central ac units, electrical, any recent updating in kitchens or baths.

You can get rid of many of your annoying little 'old-house issues' by buying an existing house that needs repairs and literally doing everything: new plumbing, new electrical, new drywall, new roof, etc....

My wife’s stress level has been through the roof.

House was built in 2005 so haven't had too many expenses recently (replaced water heater 2017 and HVAC 2018), but it will need a new roof in a few years, I would guess.