There are many seasoned investors & agents on BiggerPockets that are extreamly intelagent, and have many resources to get you where you want to be.

Being that VA Loans require 90 days of seasoning, I will have to hold tile for 3 months before selling.

Also, do not hire a CPA that recently let go all their staff members during tax season.

We will most likely purchase a vacation home that has a good rental history, so it will probably be booked for the 2017 season. 

Also, if you close on a property in Georgia the first week of deer season, put extra time in your spreadsheet to get contractors out to your property:)

Sometimes you may have to wait 6 months for the note to 'season'.

Depending on how long it takes you to go from eviction/cash for keys to rehab and renting, to seasoning the property for refinancing, you might have challenges obtaining the rate and terms you're underwriting at.

@Kenneth Futrell The first question a good realtor or seasoned seller is going to ask you -before they spend time researching and driving you around is, "How are you going to pay for this?"  

I was originally planning on jackhammering it out myself, hiring a dumpster, and replacing the structure with a basic 10' x 10' paver patio and seeding the remaining ground for next season.

As you progress you may have lots of other options but there are a lot of "seasoned" people that use hard money.