So, for a typical 2 BR condo in Waikiki (condos from there to Chinatown get the highest rents):
The rent varies between $2600 and $3100 per month
Let''s say you pay $475,000 with 20% down. Your loan is $380,000 with $95,000 down.
Approx monthly costs:
Mortgage - based on your credit = $$ ? = let's say $2500
Maintenance fee - $450
Utilities ~ $200 (phone/DSL, water/sewer)
Taxes = approx $3/$1000 of the assessed value, lets say $125/month
The transient accomodation tax = 7.25% (let's use $3000/rent) = $218. If you can hit the 6-month mark and still get substantial rent, that is a big help. (Nov 15-Mar 15 are peak rates)
General excise tax of 4.5% = $135/month
$2500 + $450 + $200 + $125 + $218 + $135 = $3628
Income = $2800 average (many people charge the 7.25% and 4.5% taxes to their tenants)
Depreciation = http://www.irs.gov/publications/p527/ar02.html#d0e2483
+ your other write offs for rental property
Now is where you should talk to a CPA based on your Adjusted Gross Income.
Last but not least, there is a tax called HARPTA (if you are not a resident of Hawaii)
It basically allows the escrow company to withhold 5% of the sales price until you fie your tax return and pay tax on any proceeds.
I know of a few well-priced 1 bedrooms inside and outside of Waikiki. Email if you would like details.