When should I incorporate a Tax Advisor?

[Emily Chapman]

When should I incorporate a RE tax advisor? I currently only own 1 primary residence. I'm house hacking it (STR the finished basement on airbnb) and I want to add another property this year. Just spoke to a really knowledgeable tax advisor (he specializes in real estate) who I want to work with in the future. $5k for his services for the year. I don't think we qualify for the STR loophole based on our current set-up. When should I get started with him? Do I wait until I have 1 or 2 properties under my belt or do I hire him now and the tax strategy will help my property evaluation?