The worst experience we've had was with a flat roofer (very common roof type in Chicago) we finally wrapped up, after waiting almost two years for them to finish/fix something. 

Then roof starts falling. 

If before getting a permit you have to dance around for Code Dept officials/ city gov and crime is thru the roof, investments will definitely be low whether real estate or other, but it should be benefiting the city officials to keep things that way.

Ex:  A roof in my area cost 9,000 and will last 25 years.  9,000 / 25 yrs is $360 a year. 

Amortize your major repairs (roof, hvac, built in appliances) and add an estimate for small maintenance.This feels not terrible to me.

I also want to clarify that I do still keep a decent amount of cash - just not enough to cover every single property roof at the same time if that ever happened for some reason. 

If you have a slow leak...coverage is less likely especially with aged plumbing.To the original poster, Salil.  

The important things to consider about HOA fees is that they usually include some utilities: Water/Sewer, Trash, sometimes shared amenities like gym, clubhouse, pool, and they are saving you the time and headache for property maintenance: lawn care, tree timing, roof, siding, etc.

I then hired contractors for plumbing, electrical, roofing, and HVAC upgrades.

I would at least recommend you have them shop a policy for you.One thing we did note is that with hail damage to roofs, they seem to be decreasing coverage/increasing deductibles on that if ever needed.