I guess my question is too, do I need invoices made for all of these repairs and damages or can I just list them itemized since my dad and I did most of the repairs. 

Here's the lowdown:Time Logs and Calendars: Keep a record of your work hours in the real property game, it'll come in handy in the unlikely event of an audit.Contracts and Invoices: Hold onto those contracts and invoices like they're gold.

After a few phone calls and emails they said they would remove the $2000 and send us an invoice in that amount.

Are you manually creating invoices in something like quickbooks as I am doing now?

However -- the caveat is that we must have basis in the unit of property to depreciate.If this was a regular trade payable, in which the contractor finished up improvements in December and sent you an invoice net 15 or net 30, and you paid in January, you likely don't have basis in the improvements.However -- let's say the contractor needs draws or needs the work paid for in December. 

When a guest gets the quote and/ or payment invoice, it will show up as "Tax."  

I have a general idea and ask a trusted trade to do the work and give me the invoice. 

Usually I get a call if there is a problem with the statement or an invoice.

We use Intuit Payment Network, you can send out e mail invoices and it only costs $.50 per transaction and takes 1-2 business days to be deposited.  

Bills, income, expenses, scans of invoices, notes about issues with tenants, the whole thing.