I would consider an alternative structure if possible.

No sane person would not consider an investment in STVRs a business.

Might want to consider an easier one if this is your first time.

(In some jurisdictions, a landlord cannot consider an arrest that did not result in a conviction.) 

Consider an addendum to the lease contract extending two weeks. 

@Zach Schwarzmiller If i were you I would consider an upgrade sooner rather than later.

It falls more in line with what I would consider an opportunistic strategy vs. a value added strategy.

Here is some hard data from what I consider an aggressive portfolio.Prosper Notes:Total active notes: 423 Current: 406 Past due (1-30 days): 9 Past due (31+ days): 8 Payoff in progress: 0Total charged-off notes: 53Total notes paid in full: 226Total notes sold: 8Prosper Returns:Overall 8.50%2015 11.79%2014 8.98%2013 10.07%2012 10.08%2011 (Prosper Dark)2010 4.13%2009 7.79%2008 7.91%2007 1.68%2006 6.86%Lending Club Notes:Total notes 413Not Yet Issued 14Issued & Current 282In Grace Period 3Fully Paid 76Late 16 - 30 Days 2Late 31 - 120 Days 7Default 2Charged Off 27Lending Club Returns (NET Adjusted):Account 1 - 11.29%Account 2 - 7.53%You can see that Prosper has proven itself in my mind and my returns have increased as I've learned what types of buyers I prefer.

a) Avoid any unnecessary costs as a beginner b) Get a few properties under your belt first before you consider an LLC. c) Consult with a good real estate CPA (not all llc's are equal)d) happy investing !  

Beyond that you should consider an umbrella policy - it is a policy that kicks in after you have hit the limit on your primary policy.