A total loss will protect only the mortgage lender, not the owner, if the coverage level is only equal to the loan balance.

How do I prove I drove a total of a1000 miles last year for the LLC?

@Zack KarpOk, so here’s a few numbers to illustrate:- 203k to purchase a home for $50k- another $50k for the renovations for a total of $100k- $3.5k downpayment. - ARV is $200k

@Patrick Menefee  Another point to mention, make sure to include at least the following, when determining the total return: Principal paydown (use an amortization table.. you can find a million on Google) or forced equity/appreciation of investment.Rent Cash Flow (CF) after payments/taxes/insurance.Tax Shield (if you are a higher income earner, this can also be something as well).  

Otherwise, unless I'm missing something, with just a slight $10k decrease in total borrowed amount why is the payment so much lower? 

You identify the original purchase price of that roof as a percentage of the total acquisition cost.

It caused a ton of water damage and mold totaling 15k.

Average demolition in Boston is about 12K, so in total this project would run us around $300K-$350K not including purchase price.

The house you're talking about with the 5,000 sqft is in need of a total rehab. 

The whole idea is to get in "light" - with as little cash out as possible.Purchase price: $80Kdownpayment: 20% ($16K)seller gives you $30K rehab creditCash at closing: $14KOwner 1st mortgage: $64K, interest only, 8% ($426.67/mo)Maybe negotiate to refi in 2 years or 1 year with a one time extension of 12 months with a 1-year advance on mortgage payment ($5,120).With that mortgage payment, and if you can indeed rent both units at $825/mo or $1650/mo total, you will cashflow from the deal even with the 50% rule.I would suggest though that you put the deed in escrow to be sure the owner does not walk out on you and get your downpayment and a renovated property at your expense.