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.  

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.   

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.I would also recommend looking for a accountant willing to work with you throughout the year.

There are, of course, also things like politics and tax policies preventing the New York side from developing its tourism sector to be on par with Ontario... 

During the GFC, the Obama administration took control of these entities and they have since been 100% controlled by the government. 

So the actual tax bill is going to be impossible to predict without looking at the individual owners' personal tax situation.How much of a gain do you think you made on your first flip?

Our dollar is losing value so you need to be with a solid operator in institutional assets that cashflow in markets while hedging inflation with tax benefits. 

If you don’t pay the tax when you transfer the stock to them they’re going to owe the taxes on your gain and you haven’t really “paid them back”. 

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.

. - Fortunately, our transparent systems allowed the owner to catch it:)- Full transparency - we would have never caught this honest mistake:(An owner also needs to be involved to approve & fund large expenses: maintenance, property tax & insurance payments (if they want to be more hands off), evictions, etc.A great PMC should also have a chat with you annually about your future plans for a property and your portfolio.