I generally advise my clients to skip properties that are near main street traffic or commercial buildings/stores.

Knowing this, its a numbers game and you will have to build out a buyer list of individuals who meet one of the two categories I noted as those are your buyers. 

Remember that many apartment building associations (especially co-op boards) will have requirements for acquisition and subletting.All the best to you on your journey!

We just started using Baselane, and perhaps we could lean on that more to be able to track the expenses, categorize them per property/per tenant/mark as 'tenant expense'/mark as 'tenant reimbursed' or 'tenant unreimbursed', and then create a security deposit balance report, that would pull everything together.I'm just looking for advice from someone that has already figured out a simple and standard way to handle this.

I started making YouTube videos and using QR codes for the toughest things guests struggle with.

You could start reporting her late to the credit bureaus(it would get reported once it's 30 days past due), that might get her attention.

Much cheaper to maintain and on the electric billand etc.I only build cabins in the woods though so again, the drainage would be the issue if you are more in a neighborhood or something. 

Do you think that would outweigh the potential of trying to build my IT business?

I plan to build a duplex with approximated 800 sq ft units, 2 bd 2 baths each.

What assets: real estate/land, buildings, water rights, licenses?