FHA & VA allow for a "Change in circumstance" for example you are moving, changing jobs requiring new location, new school, enlisted military, divorce, other life circumstance outside of your control.As far a penalty due to no intention as using from the start of the application.

There is so much to cover you kinda need to drill down for us.First thing I would do is check VRBO and AirBNB and see what is renting in the immediate vicinity of where you are looking.

So, perhaps the buyer has little cash which is why deposit is so low. 

Last thought is that it is so much easier to get one on your primary residence vs on an investment property. 

Keep that team busy and sticking with you.The chances you find a team right NOW with your 1 house with them wanting to work with someone new is so slim.

A lot of brokers are not even aware of what rental arbitrage is so maybe your broker understood a completely different concept.

As far as condos, they'll be either warrantable (meaning they conformm to conventional standards) or non-warrantable.

All I am saying is stay away from Section 8 as far as you can. 

As far as buying your first place in Hawaii, while it can be done I think I would start mainland.

Where do you think we get the saying if it ain't broke, fix it until it is.... So