There is also Island County (Oak Harbor) that has a great rental market, partially due to the military population.

I've seen monthly stipends range from 1500-2800, specifically looking near the military bases, medical center, and airport. 

The driveway is 'Y' shaped, very narrow from the street to the back, then both houses have their own parking area in the back.The issue he is having is the other homeowner is 'accidentally' leaving nails, screws, and other puncture problem items on the driveway with alarming regularity.

The VA would need training on ins and outs, policies on your leasing, maintenance and all other items in order to properly handle, communicate with your tenants and prospect tenants.

I'll skip over that and give a very brief list of some other items I tell my students in the Airbnb class I teach here in Denver.

But the items that are specific to financial performance and the safety of yourself and the neighbors, etc should be the ones you pay more attention to.  

@Sean O'Keefe how "timely".Sending owners an Annual Owners Statement with line items that correspond to Schedule E is not difficult.

The primary reason I am looking into this option now, is to prepare for future scaling as well as prevent items from falling through the cracks.

I took off a couple of items, and a little negotiating later, we settled on $300.Also, some guys think all landlords have deep pockets. 

I do not have any imminent capex or big ticket maintenance items (fingers crossed!)