@John CookYou're asking this on a forum which features over 20 tax professionals specializing in real estate.

This is as much to keep accounting and taxes easy as it is anything else.

Other than that it's all goal dependent, do you want cash flow, stack big checks, and create tax savings?

I think I am looking for someone to do taxes and give tax advice but I am 52 with a great job and would like some advice for investing / retirement planning. 

However, I'm looking for recommendations for a tax professional/CPA in the Seattle, WA area preferably the Kent, WA area.

Seems like I'll get killed with taxes if I invest outside of SDIRA.

@Basit Siddiqi the OP just clarified their LLC is taxed as an S corp...which seems like that may be the clue for why this transaction may be taxed?

Anyone have a good Tax Pro in NE Ohio that they can recommend.

They handle payments, payoffs, and year-end tax information. 

Or in other words, the rent received from house hacking would cover our housing costs (mortgage, property tax, insurance, repairs, utilities).Upon research however Oahu seem to be a high cost and low cap rate area similar to SF where we currently live.