I'm trying to help a friend navigate a creative loan to buy his current rental house and capture some 'free equity' while keeping the stability in his son's life that he has worked so hard for.Brief backstory:  I've known the guy since middle school, never really close friends, but we've stayed in touch through Facebook over the years. 

Right now the rents may be a little low, but I'm not increasing, because people want to stay.

If you plan to stay in cash on the other side of the balance sheet you can use the two to blend a much higher ROI than simply going cash without the 1031. 

Buyers will face competitive conditions this season due to continuing inventory depletion carrying over in March housing trends.While there has been a slow down at the rate that total listings are staying on the market, 36 of the largest 100 markets in the country are still seeing inventory move at least a week faster than this time last year, according to Vivas.

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!