What proof is required when I enter my expenses on TurboTax? Will I be required to upload every receipt? Is there away for Quickbook Self-Employement to communicate with TurboxTax when I am filing my taxes?

No.  Just keep your receipts as backup if the IRS asks.

There is only one way to get data from QuickBooks Self-Employed (not the same as QuickBooks Online) into TurboTax Self Employed version  at this time -- sign in to QBSE and look for a TurboTax access point from the Annual Taxes page (there will be others, but this is the easiest to explain).   You can export data from QBSE -- there is not a way to start from TurboTax and pull in QBSE data yet.  

How to export your QuickBooks SE info to Turbo Tax

https://ttlc.intuit.com/community/entering-importing/help/how-do-i-send-my-quickbooks-self-employed-tax-information-to-turbotax/00/26726