It's probably best to get a few local repair estimates from workmen who do this for a living.Make sure they are licenced and have insurance, plus go in person and check some of their past work and talk to their references.Good Luck!

@Philip Romano I actually read most of what you wrote, and congratulate you for committing to becoming FI .Like @Matt M. said you'll need two years of consistent commissions as an Agent in order to qualify for financing.My suggestion would be to keep the licence, but start another w-2 career path altogether that pays decent base, but with scalable commission opportunities. 

@Jonathan Yeh  Once you find out the costs to have the basement suite licenced, it will give you a better idea. 

@Lisa GauffShort term rentals are illegal In hawaii without transient licences.

Thank you for that advice I will have to look more into getting licensing what is the biggest difference between being like a residential agent or commercial agent . do they require different skills/licence  

Host must also notify the neighbours and apply for a special licence and renew it every year.

I have been looking into obtaining my real estate licence as i start my journey and would love to chat with you!

I'm actually getting my sales licence in a month or so where that will come in handy. 

@William KazenasYour best bet will be to buy a condo unit and apply for a 'Type 3' STR licence.

I'm starting with the goal of getting my real estate licence and then maybe being a realstate agent for a while.