Which is a wiser decision: Pull money from my retirement account or use the equity from my principle residence? 

Keep separate accounts for personal and business, and talk with your attorney about an LLC or corporation and the differences in paperwork needed and tax implications for each type of filing.

My annual vacation rents are 25%+ of purchase price and 3x what a standard monthly rental would generate.

Account Closed, you're not operating on a time line.  

The appraisal took this into account subtracting 15K per sale for an average Adjusted Sale Price of:=$320,347Even though my property was listed as Superior Upgrades along with 3 of the comps.

Without knowing the specifics of how you are spending it it's hard to say if it will offset the penalty you would pay from your retirement account.

Be careful to account for this.Rehabbed properties (with proof of repairs) and regular properties without title seasoning problems can also be set up this way – with much better scenarios than the ‘flipping’ example above.

Be careful to account for this.Rehabbed properties (with proof of repairs) and regular properties without title seasoning problems can also be set up this way – with much better scenarios than the ‘flipping’ example above. 

I believe you have to register with FEMA first, then you will actually get assistance in the form of a loan from SBA at https://disasterloan.sba.gov/ela/Account/Register1 My friend and colleague @tami dubose is going through the process now and she's the one I got the link above from.

At the initial closing, we placed $10,000 into a Mortgage Insurance Escrow account.