I have no personal experience of it, and I would welcome feedback from other HNers.
2. Your money is cheaper than your time. Spend money.
3. Conclusion: spend money on commercial software. Xero or Quickbooks. I prefer Xero. (Think of Xero as MacOS and Quickbooks as Windows in the commodity bookkeeping market).
4. Take a simple bookkeeping class or read a book so you understand the concepts. Then you can hire someone to do the grunt work.
Disclaimer: I eat this dog food.