I know these dogs and they are very well behaved and I personally wouldn't mind living them.

They've gotta be having the same issues and if you stay in communication and coordinate efforts (especially around lighting and requesting police patrols) you can make the neighborhood unpalatable. 

Selling should be the last option Like others have said , the PM companies could just be having a knee jerk reaction and telling you to replace a whole roof when you can repair it

She would stop, it would auto sit.She went to the bacon area and browsed, the dog calmly set next to her ignoring the tasty bacon easily within reach.Some veterans help group gave it to her--their logo was on it's vest.it behaved very well, and just leaned into her at all times walking or standing or sitting--always touching her leg.I had no doubt this dog was a legit ESA dog, and would never have questioned it.Plus you could tell from her overall composure--she needed it.It was just a medium sized friendly looking mutt, nothing special--and not a pit bull.

My only requirement is that I am allowed to bring my dog, who is house trained and well behaved.

I realize I have a few options, 1 would be having one of my tenants do the snow removal for a $50 break on the rent.

What I want to know from this is, am I being taken for a ride, or am I behaving naive and unreasonable?

she will fight you tooth and nail if you keep her.I think in your case, the relationship may not be salvageable, i.e. you won't be able to gain control since she already got away behaving this way, easily. 

In this example the contractors obvious racism would not likely have a negative impact on my business leaving me to select based on all other factors.If I did however hire him I would be having a discussion in advance regarding his attituded make it crystal clear, on the personal side, that  he is to keep his opinions to himself on my property if he expected to be paid.

Our worst ever tenant was rude and badly behaved at a meeting before moving day.