It is amazing how many times I have seen the cash flow represented as rent - PITI and to compound the issue they did not realize the ADU would increase their property tax.   

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

You should speak with a CPA and a tax attorney to be safe.Regarding your thoughts about 1/3 equal splits - sounds good until you check out the cost of getting a DSR rehab loan or borrowing hard money.

I let both of those properties just go for tax's I tired of the BS..

That’s $30k in taxes. 

Then you can do a 1031 exchange or sell it at a lower tax rate. 

Summit county (Akron) has a much lower sales tax rate (6.75%) than Cleveland (Cuyahoga at 8%).The MLS in Akron shows homes at similar if not cheaper homes but for a good reason.

LLC without S-Corp status will not give you any more tax advantages.

If a claim is filed and the property is owned through an LLC the individual members are less likely to be named in the complaint and that above all else keeps the members name out of the docket.

If you are considering renting it for a minimum of 30 days, I believe you will be exempt from any short term rental rules and taxes.