It could have been caused by an old pipe or a tree root broke the pipe.

Like an arborist service I have to get once a year to keep a few trees from eating the roof alive ($300/yr I wasn't expecting on one of our duplexes). 

Can a real estate investor find a solution to this so everyone wins?

Not making the tenant responsible for maintenance and repairs (yes, there are legal ways to do this despite what your state's landlord tenant law dictates) Sometimes the biggest mistake is the belief that one solution fits all circumstances.

An attorney might even help shorten this period by asking for an immediate eviction due to potential violent activity...that would depend on the judge.The only other solution I can think of that might have avoided issues would have been to evict the tenant for possession only, i.e. for rehabbing, remodeling, repairing the unit, etc. and avoid creating issues.  

However, the way my street is positioned, and the amount of traffic and trees on one side prevents the snow from melting quickly.I'd like to start a limited HOA for my street, for the purposes of snow removal only.I have zero idea how to do this - I'd love any tips about starting an HOA.

Then consult with your CPA & attorney to utilize the most appropriate solution for your situation.

My wife picks up cheap decorator items at The Christmas Tree Shop for nick-nacks.

Money often buys solutions. 

I am just offering a legitimate solution based on my experience.