This isn't a home run, but it should be a safe investment over the long run.

There is a safe harbor for you…it’s just 110% of prior year since you’re over the $150,000 AGI.You can also base on 90% of current year’s taxes to avoid the underpayment of estimated tax penalty.Keep in mind you can use Form 2210 along with your return to show the IRS how much income you earned by quarter and make your estimated tax payments accordingly.

I need to take steps to make sure the apartment is as well maintained and upmost safe for anyone living there. 

Hawaii, at least Maui, is super safe.

The pic w the back of the front door showing 5 or 6 locks doesn't convey a good look of safe neighborhood or any attempt to make a door attractive.2.

I'm simply planning to buy the homes in working class, relatively safe areas, fix them up well and furnish them and rent the rooms individually to make minimum 1.5-1.7 times higher than normal rents by including their utilities.

There is even a safe harbor from the IRS in Rev Proc 2008-16. 

Since a WL policy is generally very safe, the LOC LTV will be high.

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What are the things we should be looking at to facilitate efficient and safe collection of the revenue and depositing it into the bank?