The last time I checked, the IRS expects reported profit in 3 out of 5 years.....failure to show a profit with that frequency could result in an audit in which all claimed deductions could be disallowed and you would be forced to pay the unpaid taxes, plus interest and penalties. So.........choose the tax write-off approach very carefully.
Your dad is correct, but it is more complicated than he may realize. There are certain ways around this.......as an example, as a songwriter, my creative works can take years to see commerical success, so I can to some degree work around the "business must make a profit" requirement. Plus, I generate music income from gigging and doing session work.......so my running a studio income is only a small part of the income I sclaim to offset deductions for gear - and I also pay a lot of taxes from my day job income.....thus my tax returns probably don't fall into the "red flag" catagories.
This is simply my opinion (worth nothing) - but for a couple of small projects charging $20 an hour............I would keep in "under the table". If you do good work, word of mouth (which is very important in the recording industry) can spread and you will develop the name you desire (at least in the musical network of the people you work with). However, keep in mind, if you don't produce good product, a negative rep will spread.....even quicker!!!
If you do get a good rep and more work starts coming in............at some future time you can always revisit any decision to file for trademark protection, file taxes, etc. etc.