Also, in general, would an appraiser likely aim to provide favorable results to keep you as a repeat customer?

Here’s the REALITYWhile I compliment you on your ambition and drive, lenders want the borrower to have their own cash in the deal, not borrowed money for down payment.  

I could cash flow $300/month at the rent I'm asking for on Marketplace (I listed it higher than I thought I'd be able to get).

Not to mention cash tenants these days are ridiculously high risk!

It just cash under the mattress or something else that cannot be sourced where you have to wait. 

Either, proceed with a value add approach and structure a refi/rehab short term loan that provides renovation funds in order to reposition the property and push rents.

You will want to make sure you are installing something new that provides the right solution not just putting back something that matches but doesn't do the right thing in the first place.You may also want to consider rain gutters because doesn't look like the roof has much of a drip edge. 

It is still possible to have a positive cash flowing property but you have to be smart, run the numbers and hunt for the right deal.

Purchase price: $1,170,000 Cash invested: $900,00016 Unit Value-add property we significantly renovated spending $35k per unit doing interiors, exteriors, and amenities.

Should we sell the Red Lodge house and pay cash for another rental, albeit in a lesser market?