Leaking toilet with ceiling repair needed, another leaking toilet with sub floor repair needed, some new windows needed, new AC needed, a bunch of small electrical work, some roof issues due to ice dams that needs to be fixed, asphalt and garage foundation repair, gutters needed (none).

This reminds me of the hockey analogy "A good player goes where the puck is while a great player goes where the puck will be."

:>)I like to compare out investment strategy with hockey: "A good player goes where the puck is while a great player goes where the puck will be."

He can cloud title till Eskimos buy ice from Florida or until a judge rules.

Tenant cannot pay rent, mysteriously slips on ice, and asks for 20k from insurance. 

Are there any options (such as refi to pull some cash out or HELOC) in order to break the ice and get started in real estate investing?

I write into my lease rules that the tenant is responsible to keep their front door/walk/stairs free of "snow, ice and debris".  

Boston  requires the following:DO: Remove snow, slush, and ice from sidewalks and curb ramps abutting your property within 3 hours of snowfall ending (or 3 hours from sunrise if snow falls overnight) as required by law.

Some say appreciation is just the icing on the cake.

Florida will be selling ice cubes to Eskimos before that passes!