Kirk R.,
I am a active duty and have three homes, all rented out. Some quick answers your questions;
*Struggle with just buckling down and paying off this mortgage because I would sleep easier at night.
-> Interest rates are the lowest you may see in your lifetime. Think about getting as many homes as you can now...it will cost you less if you are using mortgages.
*Make sense to get a conventional loan - thinking PMI would be too much vs. VA loan.
-> I would work the numbers before you purchase another home. Look into pulling just enough out of your current home with a conventional refi that you don't need PMI. With that pulled out equity use that for a down payment on a conventional loan on the new rental. I would save VA Loan for when you really need them.
*Since I already have a conventional mortgage will the VA give me a mortgage and pay off the conventional of course.
->I don't understand why you would refi INTO a VA Loan? You seem to have enough equity in your home and it is a primary residence for you...why not refi with another conventional?
*How much are closing costs on a VA loan? Any way to lessen or get around some of them? Any way to get around the 1% origination fee?
->I have never gotten around the fee, interested to hear if anyone else has.
*Once I did pull out the $25,000 to $65,000 in equity would you suggest I just do 20% down? Or use the whole amount to try to buy one property for All cash?
->Work the numbers to put down as little as you can, keep a cash reserves. Repairs, vacancy, etc...
*Any suggestions on how much money to keep in reserve if I did buy a rental?
-> Consider the area, home repair status, vacancy rates in the area. 3-6 months of mortgages cost is typically time to find a tenant.
*How long would the loan take to come through?
->I am in a refi right now with same lender on a rental home...taking up to 60 days. Every company is different...call around.
*Do you think it is better to buy around Holidays vs. When kids just got out of school.
-> Research the area. Summer is generally the big move time so more should be available. Just target a home that meets your needs, ie condition, rental income, area, etc.
Hope some of these quick points help. I am always around to help with veteran questions and angle on investing.