With a good property management company, I am quite comfortable not being across the street from it.

That combined with a price list my wife and I made for materials makes me feel comfortable with the number. 

In the end that comfort level is a deciding factor.

Some people are comfortable having their rentals channel straight through their personal tax returns into their schedule E without the LLC shelter, and some always end-up purchasing the property from themselves with their LLC and position themselves that way.

I've had several roofers out but they seemed out of their comfort zone with that type of work.

Not too familiar with that, but would be a lot more comfortable with Sub-2 transactions if the DOS clause went away...

Hi everyone,  I want to give everyone an idea of who I am, and what I have going on, and I would love to get some advice on what you would do if you were in my shoes. 

Who is comfortable with a nice profit spread.

You should plan to "study" the real estate market for a minimum of 3 months, maybe 6 or more, until you get a decent comfort level.

These are some questions I would ask if I were in your shoes.1) What year was it built?