I will likely move to the island before my wife is eligible to rotate, so there is a chance that we could wait until I get there to start the process.One question I have, is it common to have to stop construction a few times throughout the building process to seek new permits?

It is also nice to rotate through a fairly small number of keys. 

For instance, what if the tenants see a big issue that you cannot immediately service and elect to pay rent over to the court causing you to experience financial strain or even default on your debt obligation?

Also, think about a longer STR to start if it will carry you - like a 13 week rotating nurse or others who need to be in your area for a month or two.

It strains credibility to say you would occupy therefore they won’t give you the benefit of the doubt that you’ll occupy as your primary residence.

We are also discussing on how to file for taxes as this one partner will claim the taxes this year and the pla was to rotate between the 3 families.

The lender themselves use outside companies (in most instances) to rotate through appraisers randomly. 

One thing we are considering is renting spare bedroom(s) to students on their rotations.

Learning all of that ahead of time will save you a bazillion headaches and potential financial strain later!

If you haven't acquired previously, caution not to attack on multiple fronts right away...one at a time, learn from it and improve as you go...we are 1000% better equipped to acquire from the prior experiences...they do take time after acquisition for dust to settle and for you to see the effect as well as what strains it puts on your existing processes and infrastructure.