Greetings @Sean Patrum,  I am also located in Charleston, SC and own my own business in the food service industry.  

I provide a service that can only be installed in new construction MDU development. 

The bank will let your monthly debt service be up to 45% of your monthly income. 

Amazon Web Services had a 15 hour outage last year.

I don't know how the Service would like a scenario like that.The most common scenario we get with situations like this is that if she can be patient, then she moves out of that house for a year and rents it. 

My Smart Move is pretty decent service. 

What is usually done on pre-foreclosure services you make a price which includes their balance owed whether it is County Property Tax, Mortgage payments, or somebody else. 

Option 2 will cost you attorneys fees, filing fees, service of process fees, etc.... some of these can be collected on the back end if you get a judgment, but the attorneys fees typically aren't collectible. 

If I replace it now while living in the house, can I begin depreciating the remaining life of the roof when I put it back into service as a rental again?

Market CAP Rate: 7% | Mkt Rents: $1100-$1200 | Duplex: 2 2BR/1BA Units Pro Forma Numbers GOI: $28,800 Effective GOI: $25,920Total Expenses: $10,400NOI: $15,520Debt Service: $12,427  Based on$165,000 Purchase price. @ 20% Down 5% Interest 30yr Amortization Cash Flow: $3,176 CAP Rate: 9.46%