While no formal laws say this is restricted, we are getting notices saying the request is not feasible due to XYZ concerns.

There are a lot of LL advantages due to the low vacancy rate.

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.  

Nice, but confusing.Our situation: FICA for kids turning 18 while working for us.So, the only thing we can conclude so far is that the age definitions in the tax law are wildly inconsistent and unclear.

@Nicholas Haubner Contact Montvale's tax assessor and building department to see it is currently classified. 

This is relevant for multiple reasons 1) appreciation is where the real wealth is generated in RE 2) real estate has tax advantages over cash flow 3) in CA property tax increase is capped.  

Reframed entire first floor to due previous fire.

I think a good tax person is worth their cost.  

And then buy a few SF homes in good school districts, probably outside of Milwaukee County for lower taxes.

Taxable income is not cash flow.There are a myriad possibilities for taxes.