Retirement tax questions

That's starting to sound a lot less casual and a lot more like a self-employed situation.  You need Turbotax self-employed online, indicate you have a self-employment job as a handyman or contractor.  You won 't have a 1099 but you can also add "other income not on a 1099".  Schedule C reports your self-employment income and business expenses, the net income (profit) flows to schedule SE to compute self-employment tax, and it also flows to the form 1040 where it is combined with your other income, deductions and credits.