Austria, Germany, Luxembourg; these immediately come to mind as "ancient" developed areas in contrast to the "infant" that is USA, and they seem to be doing very well, very efficient, very well setup and established across the strata's. 

When you have a new area that still has easy access to an established city, it can flourish. 

Of course when doing the 1031 exchange your basis will carry forward into your replacement property.Where you have a potential issue is establishing your intent to hold those properties but immediately selling one or more them as soon as you have them ready. 

Use STR-specific insurance to protect both parties and automate operations with platforms like Airbnb, TurnoverBnB, and PriceLabs.Taxable income from the STR must be reported, but you can deduct related expenses like cleaning, utilities, and furnishings.

The reason I ask is that knowing the fast movers of the area may help you choose your project.Lastly, what kind of renovation budget have you established, and is it an upfront budget, or will you be contributing to it over the time that you live in the property and renovate it? 

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

I told everyone about it for three months, then one day, an agent came to me with exactly what I was looking for and it was one of my best investments.Spend some time learning to manage well.

Overall I think the average hotel/motel is not doing well right now. 

For each property, I have a few accounts including a high interest earning savings account for reserves within the platform.

This community is full of knowledgeable investors who are eager to share insights and experiences to help you on your journey.To make the most of this platform, I recommend asking very specific, detailed questions.