Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

If you cull anything from the feedback, it is that each county (there are four in Hawaii) regulate STRs differently.

Hello @Hudson Filippi FHA does have a One Time Close construction loan that will allow you to build a home.

Quote from @Kyle Hess: I'm building a list of tools you could have handy while touring a potential fix-and-flip. 

I purchased the property from the Shelby County Land bank. 

The primary issue is that building small unit in a single count is some of the most expensive development.In addition, in most jurisdictions the primary unit will become rent controlled (assuming more than 15 years old).  

I’d recommend starting with rental arbitrage to get your feet wet and generate some positive cash flow.While I haven’t personally done rental arbitrage, some of my employees have, and they found it to be profitable.However, as a long-term strategy, you’re essentially building your castle on someone else’s land.

I am from out of state so wanted less maintenance in the short term while I build my portfolio and grow to the point where I am comfortable hiring a manager!   

If house hacking isn't the best option for me, how would you recommend starting out to build up some investments.

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.