Then figure out a standard of living your comfortable with and that will tell you weather or not single family or multifamily is the correct route for you.

I generally advise against townhomes and condos as the HOAs can become harsh and limit your options.

It's a harsh reality. 

Considering you have just bought this property and inherited the tenant, I would also consider finding some ways to be in good standing with them before proposing the rent increase, they might not take it so harshly.

This also showing up in the winter, and the crack closes back up again in the nicer summer weather!    

This is usually too harsh for a single incident, particularly with a new tenant.2.

You could try to weather the negative cash flow and refi later.

Even if I raise it from $600 to just under $1200 in the span of a month the tenants have no where to go because I will still have the cheapest rent in a 5 mile radius.Though, I don't want to be too harsh as I have been in their shoes before, I will work with them on the rent raises.  

my main goal is to just get the roof in before weather gets bad.is there anything I can do aside from a 3k escrow holdback suggested by my agent to prevent getting burned?  

Much Better weather which helps limit some of the wear and tear on homes.