@JD Martin "So poor my stories make most people cringe"  Dang!

The only communication between them and myself would be an invoice at the end of the month that itemizes all expenses and revenue.I was hoping for something less invasive, like checking up on the property after every guests' stay and letting me know of the property's shape.

They do the title search (yes, they use a title company), create the deed, handle the invoices (paid repairs to property get credited to either seller or buyer), and conduct the closing and deed recording.I've heard it works differently in other states.  

I have asked for all these in these past only to be refused by the company>Details of work order/repair request submitted by tenantsDetails of before and after pictures for certain major repairs such as drywallDetails of invoice breakdown such as parts, labor or hoursThe company would not consult with me on any repairs except once they checked with me for a $1700 water heater change out.These are some of the recent ledger entrees: Do these seem reasonable for Milwaukee area.

When a tenant wraps up we send them a final invoice that shows what charges (if any) were deducted from the deposit and the remaining balance to be refunded, or remainder that they owe.

Is there someone that can answer your questions around billing and invoicing?

And I asked receipt from him and he gave me his own custom invoice with 8y of warranty written in that invoice.

I send the invoice via email and then let him know I sent it via text.

Receipts/invoices/that you actually spent 10k.As far as timing, we do 3 business days in and out, then wire funds next day.I believe this to be typical across the industry. 

If you'll pay your contractors via signed contract or just invoices, you won't need to worry about 1099, to confirm, talk to your CPA.