My properties are configured such that a deck would go over a driveway. 

I do more like what @Julie McCoy does.When we purchased our vacation rental, I pulled as much data as I could from surrounding rentals that came even close to ours in configuration.

I picked one out which fit my criteria (location, price, property configuration) and pitched a price to the contact.

Because of the way the land is configured, I could see myself adding another house or 2 (or duplexes?)

We are re-configuring the kitchen and main level bathroom to flow well.

It gets more expensive when you are adding foundation so using existing space and re-configuring is usually ideal.

I personally just use Excel for all my long term and short term rentals.very easy to configure to do exactly as I need to track income and expenses.

Normally, you will use an 8 ft. piece, however, if you have a higher single story roof or two-story roofline grab another 8-10 ft. piece for an extension.At the same time, grab 2 PVC elbows to configure a shepherds hook which you will add to your straight length of PVC pipe with PVC adhesive.Next, using PVC adhesive - connect the elbows to each other to create a 180-degree bend (shepherds hook) and connect the elbow to a straight piece (same diameter) of PVC.Finally - onsite, connect the PVC extension pole to your leaf vacuum blower using a piece of duct-tape to seal the gaps, and carefully raise the pole up to your gutters to either Vacuum or Blow the leaves out. 

Any good property management software should be able to do that.My "Dashboard" in RentManager tells me of any upcoming move outs/ins, lease endings etc  You can configure it to provide notice any number of days ahead of time that you want.

Single family homes offering 3-bedroom 2-bathroom configuration are most desirable.