I assume your prop tax increased 1.1% to 1.2% of the ADU cost even though the ADU only valued at $75k???

Owning makes money from cash flow, appreciation, depreciation on taxes and write offs for your taxes. 

I’m talking about getting thorough with expense estimates, factoring in property taxes, insurance, and a cushion for maintenance.

If anything it just means that initial newbie tax / buffer is going away. 

I don't see how they could, since things happen... but again, granted there is no guarantee, these companies are claiming such high averages and they have such huge portfolios and good reputations, so it makes me wonder.

You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

If they don’t satisfy that call, the broker could force a sale of securities, making them incur unnecessary tax liability.Let us know which brokers offer the best SBLOC terms.

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”. 

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.