The policies continue to perform because the insurance company loans me the cash and uses my policy cash value as collateral. 

A third analysis is replacement cost.

Nobody seems to notice that two of the three tenants were arrested and are sitting in jail or that the third tenant was living with those types of people.

For instance, an classic surface capex might increase the market value more than the expenss of performing the maintenace.

The storage unit next to the garage will also get a face lift and be turned into a workshop/studio to provide a third source of income from the property.

The storage unit next to the garage will also get a face lift and be turned into a workshop/studio to provide a third source of income from the property.

I looked at other lease agreements and they mentioned stating the responsibility "tenant agrees to perform.." etc.Regarding the snow, aren't you afraid of liability?

The headaches and maintenance expenses are not worth the additional income, so for our third property, we targeted one we could substantially remodel to a nice quality or one that was still in great condition.

I give the tenant a 3 day grace period and it’s now the second day after the third day the rent will be late and I will have to start charging a late fee.

You can lean on their expertise to guide you and judge them by performance.