If your manager is just 'keeping an eye' on things, collecting/reminding on a few rents here and there and some light cleanup while being compensated in free or reduced space rent then classifying them as 1099 subcontractor is great. 

We redid the flooring in the entire house, paint, new light fixtures along with completing a full bathroom and kitchen gut. 

As for the initial post, I would ask a few questions to shed some guiding light.

All for a sign as long as the property looks occupied...leave shoes near the front door, have exterior lighting, and at least a RING camera. 

This provides an excellent opportunity to purchase properties, make light renovations to increase both rental income and property value, and optimize cash flow.

Hopefully this gives you some light at the end of the tunnel. 

The Property Manager usually does light cleaning and repairs between tenants.Recommendations or another way to think about this? 

I am only an aspiring investor, but I am a local resident of Niagara Falls, NY and I am hoping I can shed some light on your question about the winters:) I have worked in the tourism industry in the past, my husband still works in tourism.

To deter the break-ins you need to have window coverings on all the windows, a light on and not advertise that the unit is vacant.

I may have to Teak my strategy in light of the excellent advice you provide here, Henry.