@Nicolas Lovely there is always that risk with an HOA, whether the fees are small starting out or not. And special assessments are always a risk, whether the fee is low or not. Looking at what the HOA pays for and doesn't pay for as well as amenities in the community should give you a good idea of what a typical monthly fee should be and go from there. Every property is different.
Just for clarification, what exactly is the fair bit of assistance that you would get from your insurance policy? If the HVAC or water heater breaks, your landlord's policy won't help with any of that. Sure, if a tree falls on the roof, that should kick in. But general maintenance of the property wouldn't be covered by insurance, and an HOA in a condo would do exterior maintenance including landscaping.
Bottom line there are pros and cons for both, and every investor is different as far as what they're looking for and how they want to invest. There's a million ways and as long as the numbers make sense, go for it.