[Early Plan] Guidance on 1031 Exchange and Eventual Relocation

[Lex Douvas]

Hi BP - I had a bit of an early stage 1031 exchange question I was hoping to seek the collective wisdom of this group on. 

Context: I have an investment property in CA which I'm going to be 1031'ing into a property in Hawaii. Long-term, the hope is to relocate to Hawaii full-time. We're trying to line the moves up such that we have an easy landing and take maximum advantage of tax shelters. 

Our current plan: is early stage, but I was thinking of sequencing it as: 

(1) Sell the current property (we have an offer that we are in the process of countering)

(2) Find a single family home or townhome to 1031 into. I need to run more analysis on which one would actually be more likely to cashflow. 

(3) Rent the 1031'd property for 2-3 years. 

(4) Relocate to the 1031 property and swap it to a primary residence. 

(5A) If we are happy with the 1031'd property as a primary, turn our (now) former primary residence into a rental, then continue with 1031'ing from there. OR

(5B) If we aren't happy with the 1031'd property as a primary, sell our (now) former primary residence to use the 2-yr capital gains tax shelter, take proceeds from that to buy a new primary. Turn the 1031'd property back into a rental once we have the new primary (and/or sell it and take the tax hit at that point). 

In all cases, we're specifically targeting using the 1031 as a landing pad for when we eventually take the plunge. We've got 2 kidos and pups so the barrier to actually moving if we don't have a place to land (that's pet friendly, etc) are high enough that we'd probably never end up doing it. Because it's partially an investment plan, partially a life plan I'm willing to accept less of a profit on the investment property (I want it to at least break even, but we'll try hard to find one that's cashflow positive still). 

My question to this group -- given the long-term plan of relocating, did I miss any options? Is there a simpler route (other than just doing a mid-term rental)? Any guidance or steers very welcome, including the brutally honest ones, many thanks for your time!