Traditional home owner's insurance isn't always comfortable with the new liabilities that comes with rental properties so their coverage will likely be less and the policy may end up being more. 

If it's a traditional lender (bank) the property will have to be livable.

if your area EM D are traditionally small or what have you FLASH cash works as well.. just walk in with 10k in cash and fan it at them.. leave them 500 or 1000 to sign the deal...

I am aware of some of the general financial indicators analysts use when making a decision about a deal, but, are there any others investors like or would like to see on a CMA that aren't traditionally thought of?

He mentioned that he was more interested in a traditional sale and after speaking for about 20 minutes we left off with me wishing him luck on his sale and him saying that he will keep my offer in mind.

Try to go for traditional with banking, it's less expensive and will help build your credit.

Given that what I'm trying to do is to a)help the seller get out of her sticky situation without b)needing to bring much cash to the table, and c)save funds for what will be a substantial rehab that would probably disqualify me for a traditional construction loan, are there any better ways to structure my offer?

Clear as mud?

@Rocco Swinney I wish it was more creative, but I just did a traditional commercial loan with a local community bank that was a referral from the selling broker.

Traditional insurance companies like a State Farm will force the replacement cost which could be $220K or more.