Hey @Jennifer Smith and Michael, have you thought about getting a house with a detached garage and then converting that into an accessory dwelling unit (ADU)?

We do permit vaping as it doesn't damage the property.

The income on the listing says they are getting $1,100  for the accessory dwelling unit so I am unsure how your expected income is $2,200?

Both appraisers comped it as a 3/2 and then added value for an "Accessory Unit" (+$5000 in value in 2014 and +$9000 in value in 2016). 

It also allows the urbanhouse, detached accessory dwelling unit, duplex, and tandem house building forms."

Friends in Ithaca recently added an accessory dwelling unit when reconstructing the garage at their SFR in Ithaca and the process has taken well over a year navigating the city bureaucracy - with a couple of construction starts and stops because neighbors complained (spuriously) to the code office. 

Using some of our own funds as well as the FHA 203(k), we renovated the house including an addition and converted the garage into an Accessory Dwelling Unit.

I am shooting for a fourplex or possibly something with an accessory structure.

Many area allow accessory apartments which basically sounds like what your trying to do.  

As communities prepare for an aging population, accessory dwelling units or MIL apartments are becoming more common in SFR zones.