If you are concerned with all the tenants leaving, choose to raise one per month.  

My fiance's mother lives up there and last we spoke she was concerned about her home losing value.

I think it looks cool, my only concern would be what @Chris Jenkins alluded too.

We have some concerns with considering expenses in our model, specifically with replacement reserves in comparison to general maintenance, how much to set aside for reserves, etc.Thank you!

@George Allen: I inquired about the the length of the loan process and the concern that "it may take forever."

I have gotten as far as figuring out the 25% standard withholding tax, and filing the section 216 to have that withholding done on net income rather than gross, just wondering if anyone can add some insight to the process or point to some good resources and or professionals that might help give me some insight and confidence, or point me to best practices where this is concerned.

My concern is the the "due on sale" clause being executed by lending institutions when using these methods.  

ThanksGreg You didn't specify the upside nor speak of a value add play in the deal so it's a little difficult to speculate how to best structure a creative financing package.Assuming it's a value add play with good risk adjusted gains at the end of the process then maybe the safest route is to negotiate a wrap transaction with the seller, and if your are concerned about a due on sale clause make it contingent on the lenders approval.The seller will confront these same financing scenario issues with all other buyers so if they want to sell the property then they can either deal with the issue with a reset and able buyer, you, or kick the can down the line looking for another buyer who maybe willing to assume a less than stellar financing package.As the buyer though your only concern should be the financing package that delivers you title, assuming you plan on making extensive improvements to the property, and allows you to earn what you determine is a reasonable cash flow from the project.Options aren't bankable.

Neither are my fault, but nonetheless - you are correct.Luckily for me, the property is worth more than 60k so I'm not terribly concerned about losing money on the investment at this time...

My last concern that I will most likely have to talk to bank(s) about would be first time financing under a new LLC and all that, that entails.