At what point do you need a tax strategy?

[Jacob D Adamczak]

Last year I had a W2 job, making the median income in my area and owned a house hack I had just bought. I hired a CPA but there was no tax strategy or planning and I probably could've saved the money and used turbo tax. I'm not sure if this was because he wasn't a great CPA or if it was because I wasn't yet at the level to need one. Fast forward to this year, my airbnb house hack has had a full year of operation, I've doubled my W2 income, and I bought a rental house. Im also doing some 1099 side work for a local realtor. Is there an income threshold or complexity of income where your CPA will then need a strategy to help you save money on taxes? Or tell me if I should run my 1099 thru an LLC or not?