Super motivated by his story and approach to investing.

My biggest challenge i am facing right now is that with my wife being stationed here in hawaii and myself not wanting to start my investing in such an expensive market here paired with me being a full time student right now I dont have an income.

Communication to the island has been a challenge as well getting in touch with other necessary moving parts on the island such as the notary, Kadaster, as well the previous buyers.

Are they challenging your title?

I'd challenge anyone to find a reserve study of an age established condo that is 100% capitalized.   

Certainly that's a safer approach for the buyer, but could easily put him at a disadvantage relative to more experienced flippers who can complete the due diligence quickly and make offers with few, if any, contingencies. 

Now being a new eager investor, I may have a wide eye approach but I do like to aim high.

The challenge with house hacking is weighing the aspect of 'places we'd like to live' with 'places where the numbers make sense.' 

I'm curious as to what the best strategies are for identifying potential properties, how to approach the homeowners (letter, door to door, a written offer, etc) and how to write a fair and solid price (I'm thinking full price offer based on comps minus 6% because of no commission but throwing in some cash or creditiing closing costs to the seller to sweeten the deal a little bit. 

However, the challenge with short-term rental is all the HOA regulations prohibiting rentals fewer than 30 days.Heres my question: What is your opinion on the best route to go for house hacking in this market given the constraints?