I own 32 properties myself and have bought and sold over 300, including a few apartment complexes.

Maintain - includes taxes and insurance?

If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

I was chatting with some of my lending buddies at big banks and they are all backing away from the CRE space including office because operating costs are increasing more quickly than rents.

There are clear winners in types of photos that should be included in your listing, along with examples of listings I believe achieve this.

Are there any specific clauses I should include in a room-by-room lease for a shared living space?

As for holding a home and building another one - be sure to include carrying costs of the first home while building the second.  

I would include your realtor in the conversation, at least when you're introducing yourself.

We actually CAN'T explain what we are seeing if we are operating on the "purely rational actor" hypothesis (as you implicitly observe), we MUST include highly irrational and emotional individuals to explain what we are seeing.- Investor uncertainty.

Alternatively, if you’re using QuickBooks Online with a plan that includes the "Payments" feature, you can collect rent directly through QuickBooks while staying on top of your bookkeeping