Is there any issues with doing this on investment properties that people have had in the past? 

Quote from @Jim Stanley: You should reserve insurance for large claims.Contact the city and report the issue to them.

I think that's a great approach I have a lot of clients who self manage have no issues at all.  

The letter also states the total non-rent items currently owed by the tenant, such as accumulated late fees or repair charges.Also very important, the tenant states they have no unresolved issues with their current landlord, except as listed in a space provided, and they have no current plans to cancel their lease under the Service Members Civil Relief Act or for any other reason. 

Zoning issues?

Unless you negotiate a new contract or addendum with your PMC, they do NOT have to abide by any requests/demands you make that contradict what's written in the management contract.If they have in fact NOT followed the terms of their contract, then you'll want to send them something in writing pointing out the specific language in their contract that they violated and ask what they plan to do about it.If they fail to correct or address the issues, then you'll want to start looking for a new PMC.

The issue is cost.

I can only think of 2 times inn the last decade my client has had to go though an eviction and both times it started cause the owner and tenant had personal issues. 

The snow companies that are good can be really pricey and we have had issues with some of the smaller guys in past.

It is what is left after snow removal, cutting the grass, utilities, tenant issues, parking lot issues, property taxes, mortgage payment, etc. that make a difference.