Pull out a spreadsheet and go through the tools everyone mentions to run some comparables and take note of photos, amenities. 

Great question @Lorraine Hadden,You should always compare both side by side to see the advantages /disadvantages to each.

Are there any unique considerations or red flags you look for compared to the traditional rental process?

CT isn't cheap so if you plan on doing it there you are going to surprised at how poorly you do. maybe in the suburbs I'm not sure but as much as I know people call us from CT and everyone is rich and has lots of money and things are expensive out there. build to rent is a great model. we build 3 story walk up infill and keep it to the residential side. 3 units is the most units before it's commercial and you need engineering, etc. check comparable and things liek that. we came up with this design a year ago and we sold 10 if you want to talk further please DM me happy to connect. there are some great build to rent conferences. we went vertical not horizontal with it to save on build costs and design to fit on any infill lot. this fits on a 3500 square foot lot. most lots in our area are 30x120 or 30x150. in miami where I live now they are 50x100 or so. but any infill lot we can pretty much get this one on. there are some great build to rent conferences coming up too that if you like this topic I'd recommend attending I'm sure you'd learn a lot.  

It's worth a conversation.IF you determine that selling is the way to go, $1M could buy you a comparable property in Scottsdale, depending on where in Scottsdale you'd like to be, and how much land you want on your lot. 

Multifamily projects often yield higher per-square-foot returns due to economies of scale and consistent demand for rental units in urban areas.

Even cash flow on a decent property from years ago doesn’t compare to the appreciation over the same time.I have seen cash flow investors that end up investing in Ohio or some other C or D neighborhood regret their decision after realizing there is zero appreciation in those places and cash flow won’t even cover a major expense if something happens. 

For us to guarantee a deal, it is contingent on them making reasonable effort (3-5 hours/week consistently, for example).

What is the current market valuation of the property based on comparable sales (defined as similar properties, within a 1-mile radius, within the last 30 to 180 days, that are within 10% of total square footage)? 

It’s worth calculating the total investment (purchase price + wiring replacement) and comparing it to what the property could yield after the upgrade.