Stay west of I-25 if you can. 

It is not impossible but it is definitely not quick and you need considerable time to stay on top of things.

Or for that matter you could stay together and do one exchange into another asset. 

Been reading a lot and it does seem like the numbers regarding cash flow for a single family home on Maui (right now) wouldn’t work too well.I understand and accept that passive income is for the people who’ve built a massive net and are at the top (but even then I think they have to work and make sure their system stays functioning)I really want to learn more about owning/operating vacation rentals, specifically in HI if possible and specifically the tax part of it (now with the shift of the 2018 tax laws).I’m going to dive through the forums and try find more books on the topic.

We are trying to keep our drywall guy working to stay on schedule, and wonder if anyone has a cost effective and sage recommendation on getting ~2,000 SF heated?

Keep the property in good repair and people will want to stay! 

The rest of the people will stay in their homes until they can no longer dodge the courts and the sheriff.

My question is: are there areas of Oakland that I should stay away from?

Possibly stay a year refi rent and move again..

Make it clear that they have to pay to stay (even though they really have all the power) and be really firm about holding them accountable to their side of the M2M agreement.