Leave those money pits to historic societies that don't care about money. 

Make sure to include monthly expenses for lawn care / snow removal, insurances, any utilities you'll pay, repairs/maintenance, capital expenditures, vacancies, taxes, etc.

Based on the feedback from other tenants, I sensed that I should be careful about my safety when interacting with those folks. 

When dealing with a shady handyman, that's like blood in the water for sharks.In the future, you can best prevent this by not waiting till the last minute to take care of such repairs. 

More importantly, why would they care...they don't have to live with the person. 

Additional Questions I have in my mind are: 1)This property located some distance from me and so I am not entirely sure if 5 of 2 yr dumpster pick up X 6 times a week that my private trash service company is telling me I need are indeed accurate. 2)This is a condo unit, however the Condo is refusing to take care of the retail condos' trash pick ups as the residential side is being taken care of for free by the city.

Mom is in her 90s and needing way more care, we've added $1000/mo in care assistance just this year and that is not covering a lot of care hours.

Landlord insurance in each properties as well as an umbrella insurance can take care of majority of the issues. if it arises. 

The wording needs to carefully crafted for this list.

Be careful what you ask for!