With only one can for regular garbage, it's a lot heavier than separated out to 3 cans if each tenant handles their own, and I no longer have cans, some with hardly any garbage in it, blown over and worst still, into the street.These triplexes normally come with one driveway, so the guy that handles garbage usually gets it for free if he sweeps the sidewalk.

For exteriors something like: sidewalks, driveways, exterior walls, windows, doors, grading, drainage, etc .  

Check to see if you have to install any manholes, fire hydrants, curb, gutter, sidewalks, street signs, street lighting any specific street design or access requirements, Check DOT requirements for access, stop lights and permits, traffic studies, DWQ requirements for permits, permit fees and time framesOnce you have an idea of what you can build and what is required in terms of permitting and infrastructure you want to talk to some civil engineers, architects and commercial general contractors that do the type of projects and build the type of buildings you want to build so you can get an idea of costs, time frame and requirements.This is a brief and broad overview of how the development process works what's required before you get too far down the road on a plan.

Not only was the facade in horrible disrepair, but patient access was sketchy with drop offs where the sidewalk slabs met the soil / landscaping (if you could call it that!)

A tiny bit of peeling paint, a cracked window, an uneven sidewalk and any of a very long list of defects will cause a failed appraisal. 

They now shovel all of our common sidewalks without us even asking.

One time I had a tree company damage several panels of my sidewalk, which is another reason you want them to have insurance.I have trees that are 12 feet from a house and although not ideal, it may not be worth the expense to remove.

But then down the line when a big expense comes up (roofs, patios, sidewalk, etc) then they are screwed and forced to do an immediate special assessment where each owner has to cough up a few thousands. 

We do have value add with the approvals and the lease with the MTA for the sidewalk to increase walkability which is favorable but not enough to secure a loan as-is. 

Or to walk a pig down a sidewalk is a criminal misdemeanor?