The project has already started and all phases should be done in 3-4 years.  

I have definitely benefited from this crazy real estate market.

(not a commentary on deal machine specifically b/c idk about them)Maybe others can chime in on the benefits of deal machine that I'm unaware of. 

On the other hand, Appreciation is the main benefits of Real Estate Investing.

If you/your CPA haven't leveraged the Tangible Property Regulations (TPRs) and cost segregation on these, you are likely missing some needed cash-flow and tax benefits that are available to you.

Closing costs might be higher with 3 loans; and i say might because commercial lenders charge points, and will require a phase 1 in addition to appraisal and other fees.Rates are low at the moment but 30 year loan locks them in, and in 5 years rates will likely be higher and you'll have another set of closing costs.

A realtor who does a lot of property management may know a landlord who is wanting to phase out of properties and be able to help you land an off market deal.

You will always benefit from having expertise on your team.

The goal of this plan is to free up VA benefits to purchase a new home, rent out the current home that I am in and get cash to put into other investments.Please feel free to offer any advice or critiques.

Your military benefits will give you a huge leg up over your coworkers.