I would have about $30k - $40k for a down payment, closing costs, and a few months of reserves. 

If the conditions are not good, then you've saved a lot of grief and money buying into the wrong area at the cost of a lower amount of grief and money through the sub-lease.I 100% agree, though, that extended paralysis will render you subject to the whims of a changing market. 

I am looking for a builder to partner with who will finance building costs (and get reasonable GC fees above cost for their efforts as well).

This seems unfeasible for rental investments due to the high cost of capital.

Yes, it costs a little more... adjust your offers accordingly.The law is a mirage.

All of that is independent of one-off maintenance costs - for example, trimming my palms costs $100 a couple of times per year.

This is just one of the many ideas I'd love to implement in this new build.I've talked to a fantastic builder in the area and the build from start to finish with the lot should cost about $450-500k.

Now your housing costs are $4700, but you are getting $2900 in rent.

I am looking to invest out-of-state as a long-term, buy and hold investor in the lower cost, higher cash-flowing markets of the midwest and southeastern US.

Costs to do anything are high in Hawaii so I know what you see here is not normal everywhere.