I would make sure they have great systems in place and have great communication with you.

I recommend finding a strong brokerage with investor-friendly agents who are doing a high amount of volume.You can set up systems and procedures to make it easy for them to refer your company over. and keep their clients happy.

Nobody will ever respect you for the blood, sweat, and tears you will go through dealing with all of the pain and agony of trying to navigate such a ridiculous system.

Not trying to cheat the system, just trying to understand what I'm looking as I consider real estate options.Separately, would something with an ADU be considered a multifamily?  

Let me investigate a house with your local agent and take photos of the major systems BEFORE YOU MAKE AN OFFER.

There is an unfinished basement which will likely be permitted to convert into an ADU but might trigger the installation of a fire sprinkler system ($30k).

Someone with a large portfolio might have a system that works for them and which they have maximized but which might not translate well to your market, your personality or your approach to investing.

Does maintenance factor in replacement costs of the HVAC, Roof, Glass windows, structural piping, Parking lot repaving, sprinkler systems, etc. 

Almost feel like a roll of the dice and you just gotta pray you don't run into a tenant that can game the system and this case even have more fuel to their fire since they are unpermitted. 

Similarly, I am currently depreciating an HVAC system I installed several years ago so wouldn't the remaining undepreciated amount be added to my adjusted (carryover) basis (using either the general or simplified methods) after the exchange is completed?