So we finally decided that even though we have the option now to go directly to HI and are used to a relatively low-cost lifestyle(like here we have a 2 brm condo, enjoy cheap or free outdoor entertainment like dinghy or board sailing, maximize theme parks season passes, etc) that we can live under the 90K my wife and I are looking to earn between us in HI(plus have enough savings to cover even the worst-case scenarios), the alternative of an upper-100K package for me in the mainland - plus the lower living expenses there compared to our present location albeit minus the tropical lifestyle we enjoy so much here - is too much to pass up that we decided a couple more years to pad our savings further while the iron is hot is not such a bad idea. The big difference is having my network of former colleagues/hiring managers being all in the mainland(or in Asia) and their current needs for our shared specific skills and experience vs having to go to managed service providers in HI who are recruiting for generic IT skills. It also helps that the mini-hiring spree in our areas in the mainland seem to be holding up even in these economic conditions. Judging by how fast things can go south in the tech world, it seems prudent to maximize on the trend while it lasts.
Subject to the final paperworks which we expect to finalize in a week or so, we will move back to the west coast this summer.
In the meantime, we will definitely spend most of our vacation time in HI and possibly start scouting for housing prospects as we near our target date(it would be nice if we can pay off a good chunk of the purchase price from the difference in mainland vs HI payscales alone without dipping into our savings or current assets so we can bring more savings when we relocate plus bring down monthly housing payments to what we can afford with HI salaries. It is also a big motivator to save for that vs just saving for savings sake as we sometimes tend to feel "savings" fatigue
. With our current lifestyle, no car payments as we have old cars, good public schools where we're moving, free company health club, etc, we think we can live at 60K salary level). Hopefully, having our own place in HI before the big move will allow us to do a "creeping relocation" before we severe the mainland salary lifeline.
I'll also be constantly looking out for remote working opportunities from the mainland if possible but will be prepared to start fresh in HI otherwise.
Thanks for reading this far and looking forward to those who would care to offer critiques and suggestions.