Fundraising Software Resources

I'm not sure if a tax receipt or an acknowledgement has been sent when someone donates. How many do I have to set up to make everything work correctly

With the integrations of Stripe/Paypal, we get multiple entries of donors based on how each of them pay -- if they use a credit card at an event, we'll get a new donor profile; if they sign up as a recurring donor through paypal, we'll get a new donor profile; if they get a check, we'll get a new donor profile... so its hard to keep them all in one place, especially when trying to input pledges, etc

Need to find a way to upload data for credit card reconciliation into Quickbooks to keep my bookkeeper from killing me.