I had asked this question on the Facebook fan page and got banned lolwho do you use for invoicing tenants? 

DEFAULTS Tenant will be in default if: (A) the Tenant don’t timely pay rent or other fees and charges they owe; (B) Tenant or any guest or occupant violates this Lease, property rules, or fire, safety, health, or criminal laws, regardless of whether or where arrest or conviction occurs; (C) Tenant abandon the property; ....When Tenant is in default, the Landlord has the option to declare the entire balance (all outstanding balances including but not limited to invoices, rent, cost due to damages/abandoning the property) payable hereunder to be immediately due and payable; the Landlord may exercise any and all rights and remedies available to Landlord at law or in equity and may immediately terminate this Agreement.XVI.

He just said "now I don't feel appreciated, let's settle those favors I did you before we proceed any further" and sent me an invoice for $2K for the lost materials + time with the break-ins.Overall, the job seems to be ~80% complete but with poor quality, and I will absolutely need to hire someone else to fix his mistakes.

For clients you bill regularly, you can schedule invoices to send automatically, so you don’t have to do it manually every time.

It specifically prohibits breaking a $10,000 invoice into four $2,500 invoices to get around the rule.In many other cases, there is even less clarity. 

Quote from @Jane Dang: My rental property is a single-family home.

He was always slow to send things like invoices and I've been repeatedly asking him for invoices from March and May- I still don't have them.

Quote from @Jane Dang: My rental property's roof is 20+ years old. 

If your side is legitimately so dang superior and "right" than you would NOT need to stoop to such BS.

If a tenant comes in to pay multiple charges with one payment, my office manager has to get out the pen and pad to figure and place individual payments instead of something similar to Quickbooks where you enter an amount paid and select which invoices you want it to apply to. 3.