The send shop is easy unless you go at a time when the location is busy. I would avoid beginning of the month, Fridays, etc. You have to return within 30 minutes to get the refund. Otherwise, you get it within a week.
Also much easier to upload the receipt pics if you put them into PDFs.
The awkwardness is in the question shops that don't require you to send any money. Those involve the most ridiculous questions and you have to ask twice. Sending small amounts of money isn't so strange. US$20 can tide you over in the countries used. Some meals and a cab to the airport for a friend who lost their wallet on vacation. Maybe most people would throw $50 or $100 at a minimum, but it's not necessary.