The family purchased a lakefront property in a nice area three years ago but then ran into a series of issues, and have abandoned the place because of them.They are hoping the bank allows a short sale (asking for roughly $20,000 under what is owed)Here's what's made them so unhappy:Anytime they used the laundry it was dumping into a dry well, which would back up into the house forcing them to take their laundry to a laundromat instead!!

You may want to share you analysis with a few banks and/or property managers as they will typically weigh in on your assumptions if they are potentially interested in working with you. 

@Zach Denny  Similar to what Minna posted above, I have done with a local portfolio lender bank where they set their own lending rules. 

Most banks don't really know how to do that because they cater to SFH owner-occupants. 

My first deal looks like it will fall through because the bank doesn't like my work history. (4 months as a union electrician, which the bank considers contract work).

now if you could get a seller to be the bank I get that you could smoke and mirror those deals.. but i would think those would be picked over low value or properties in the worst areas of town etc..   

Go to small local/regional banks NOT national ones.

I think the LLC also makes it easier to open a local bank account, which is convenient to pay utilities or other local bills or your property manager, etc.  

This way, I can get the bank statements for the property and categorize and reconcile everything. 

Once you hit a certain number of loans (check with your state dept of banking and finance or dept of business regulation), they might require you to have a license.