I would confirm with your tax advisor/CPA that adding your wife onto the replacement is considered the same tax paying entity.

After this refinance, we will have about 65k in the operating/reserve accounts.

Save your money for reserves.

After this refinance, we will have about 65k in the operating/reserve accounts.

(the reserves requirement is a little different for Freddie)Freddie Mac guideline:Each Second Home or Investment Property Mortgage must meet the following requirements:• Each Borrower individually and all Borrowers collectively MUST NOT BE OBLIGATED ON (e.g., Notes, land contracts and/or any other debt or obligation) more than 10 (ten) 1-4 unit financed properties, including the subject property and the Borrower's Primary Residence, provided that, when the number of 1-4 unit financed properties (including the subject property and the Borrower's Primary Residence) is greater than6 (six), the Mortgage must:o have a minimum Indicator Score of 720 ANDo 8 months of the monthly payment amount on each additional second home and/or 1-4 unitInvestment Property that is financed and on which the borrower is obligated.

I'm pretty well booked like this until January, and taking reservations for summer and next fall.

Should I wait and build up cash reserve and see what happens on the market? 

In most scenarios, military towns are cashflow markets therefore, it's easy to charge a bit more for rent (depending on the Soldiers BAH) and build reserves that mitigate the risk of high turnover.  

Thank you for confirming what I was reading about re:disqualified entities.

You have to factor in expenses as well (Insurance, management, taxes, and reserves), if that is true cash flow than that is a crazy good deal for him (36% CoC return)!