1. Schedule C top line is sum of all 1099 Misc (we get about 5-10). Twice now (2017, 2019) IRS claimed we didn't report one of them, and I had to send them calculations as to how they add up and flow through to Schedule C.
As long as you report all the income you made from all sources on line 1 of the Sch C you should not have any issues with the IRS ... you must report at least as much as the total of all the 1099 forms. Why the IRS is asking about this is a mystery if you are completing the form correctly. If you complete an accurate return then you have nothing to fear from an audit ... it is a hassle but nothing to worry about... just keep accurate timely records.
2. We submit all kids' college expenses to 529 plan and they reimburse and report to IRS as eligible expense. Again this is one of those quirks in the tax law as I already mentioned ... they questioned this mostly because they were questioning other items on the return. Every once in a while one of my clients will get a letter about this but it is easily resolved. Nothing you or TT can do to be more proactive on this matter.
