If you ARE running a trade a business - 1099s are required.

Gatlinburg and Pigeon Forge are both extremely strong right now , with most people overpaying in the years that you mentioned and simply not KNOWING OR CARING  how to properly run a top notch Air BNB. 

.- Would you be requiring custom changes often to your digital workflow?

We offer it at TFSB but it does require the basics like qualified credit score, DTI ratios - Must have W2 or (2 years of 1099 income) to qualify.

@Patrick ShepWell said @Bill B. the lending wouldn't be an issue in this case as long as you meet your reinvestment requirements.

I recently obtained my HI real estate license to access the MLS and assist with my personal house-hunting needs.Does anyone know of a more boutique brokerage on Maui where I can hang my license with minimal overhead and without the requirement of going through a mentorship program?

It is simply far too tenant friendly. 

Once the investor reached the particular sale as well as reached the 1031 exchange requirements, the investor will have the opportunity to have their taxes be delayed or postponed until such time that the recently obtained property will be sold.

This was also confirmed when I went there to submit the required documents, but they couldn't give me a proper timeline on when it would happen claiming that they were backed up. 

REPS requires you to spend over 750 hours annually and more than half of your working time on real estate activities.