Much more flexible coverage terms, single policy, better pricing, etc.In conclusion, don't look for an insurance company, but a commercial broker that will have multiple commercial companies to help you get quotes from.The problem that you run into, and most other growing investors, is the All State agent is not a commercial broker and usually does not have a good connection to a good broker.

How many hours (or days) do they spend running all over God's green earth to show houses to a buyer that can't make up their mind and then suddenly disappears and never purchases anything?

Pick a single business bank account and start running all your income through that account. c) >24 months, Fannie opens up (typically) once that 2nd year of tax returns is filed and processed by the IRS.If you do a or b with the plan to refinance once you hit c, make sure there is no early payoff penalty.

If you pay the utilities, there is very little concern for conservation  on the tenants part.. they are less likely to report leaks/running toilets.  

Run a report from BP Calculator and export the PDF.

@Joey Newton run it through the bigger pockets calculator!

Run the numbers.

Second part of the question - The "VERY BRIEF" conversation I had with my mortgage guy a week ago was "a cash out refi will be better in the long run". 

We run a Vacation Rental Hosting & Cleaning business so we have a lot of experience with Waikiki condos.

However, you still run the risk of getting so busy with your regular job that you lose sight of the rental and things slip through the cracks or you don't have time to deal with late rent or you forget to do an inspection...A property manger costs about 10% which is $2,400 yearly on a $2,000 rental.