EDIT: Also, don't write off meals and entertainment you dang realtor!

5.Are all my invoices uploaded to my owner portal?

I have no idea if you will be a good personality fit with him (and that DOES matter), but he knows his rental property business pretty dang well and his clients (I see their financials, so...) seem to certainly be doing well enough. 

Dang, 100 tix though.

Dang.

I have begun hiring out some of the paperwork tasks, such as mailing monthly invoices, but at our small scale there is only so much that can be outsourced short of hiring a property management company.

@Dan G.  

Dang!

I am not an expert in higher rents (my highest is $900 for a 3/1.5 in Belvedere), but if I had $1,400 to spend on housing every month, I'd either buy my own house right now or expect some dang good schools.My 2¢. 

If you do outsource first, I would not strictly focus on the management fee percentage (i.e 7% vs 5%) ... some of the most expensive property managers I've ever had have charged the lowest fees; 5% does not mean a whole lot if they pick your pockets with marked up repair invoices, select bad tenants that don't pay rent & trash the place, and ignore the repair requests of good tenants causing small problems to get large.