They also continue your depreciation schedule.  

Now, I expect to continually grow my income over time, even in retirement, and will be taxed higher than I am today, which ironically, creates a desire to leave my W2 so I can access the 401k balance sooner rather than later.  

Continue to watch your investment grow and repeat the process with larger apartment complexes.

Instead of continuing to build up my real estate portfolio in small multifamily (1 - 4 units),I am now leaning more towards Syndication and possibly Triple Net Lease opportunities. 

I hope that he continues to stay renting from me.

Aloha,Simple answer: it depends.It depend on zoning, it depend on NCU (you can find out if your unit currently has valid certificate), it depend on condo’s by-laws and house rules (it will continue to change).Honolulu City and Council is currently tabled several bills to regulate and taxed, we won’t know which bill passes, or continue to amend and when the bill into effect.https://www.google.co.jp/amp/s/amp.thestate.com/news/business/national-business/article229502899.html

You may want to continue month-to-month in the beginning since you haven't screened them and you don't really know the type of tenant they are.

We need better policies and understanding of the law, or tenants are simply going to continue to take advantage of us.  

Should I get a CPA to help me with my taxes this year or should I continue to use online tax tools until I have acquired more properties? 

My sector in retail is changing and will continue to so I'd like to set up to capitalize on new avenues.