I’m trying to have him see the bigger picture if he puts money in tax advantage accounts first and strategically uses a tax professional, that he will be able to offset his high tax bracket w2.

Professional SEO here with 15 years experience (who happens to be looking to get into the STR game in the next 12-18 months). 

They often partner with CPAs and other professionals to create strategies that maximize your overall net worth.

Ours are passive, professionally managed by someone else and we are fully hands off…

First page google search has his own website and the "Top 100 Professionals" bio (you too can be a top 100 professional for a mere $5,000, or maybe it is $10,000).  

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Timing schedule for materials Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I will be in Cincinnati from 11/1-11/3 attending the REIAGC this year and would love to meet with any Real Estate professionals and investors while I am in town.

That being said, a professional is necessary.

Sometimes you have to go with your gut, even your professional agent doesn't have all the answers.