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.

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

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.

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

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. 

When would I need to secure items for installation like the kitchen cabinets and toilets, etc.   

Can this be scaled to offset larger items?

I'm looking at some flips in Arizona and the math doesn't work out when you add in some of the big ticket items like a brand new AC.