My question is, will it be a better decision to put 20% down on the property I purchase in order to avoid PMI; or to put 5% down and use the extra cash to potentially line my self up for another acquisition in the near future?

But, if there is a possibility of a short fall....HOA/other debts that can't be negotiated out with the bank ( the lender will only contribute a set %) you need to be prepared to pony up some extra money above and beyond the purchase price. 

I think the advice of billing them early but giving them time to get the extra money together is a good way to proceed.

If 5+ acres then what is your plan for all that extra land, and do you have the money on hand and the local regulatory environment mapped out to execute that plan?

Making extra cash on the side is always fun.

It's more conservative and while my rate may be higher and I will pay a little extra in interest over time I can still accelerate my payoff.

I am having some difficulty determining what should be used as a CapEx value.

It will potentially give you some extra freedom.  

They even had difficulty showing any kind of income, let along the amount they needed for the house.

I have been having difficulty finding a mentor or consultant and will be attending a networking event in January.