Once you figure out the payment schemes, next you have to see what kind of resources they have to help you. 80% of real estate agents fail or only make like 40k a year so you have to avoid those people and only focus on finding a niche.

Here's the facts:- I'm pre-approved for $330K but I can push it to $450K if I really need- $10K-$20K Saved for down payment. $10K Saved for renovations- Saving $800-$1400 every month- I have access to the VA loan(*preferred) Strategy #1: $100K-$200K purchase. ~$1000 Mortgage.

Good on you for saving up a substantial down payment so you don't have to go down that road. 

That currently is my plan, I have been trying to figure out though if I am planning on putting some money down, to keep the mortgage payment more reasonable, is using the VA loan still beneficial?

I would have the current owner provide you proof of deposits for the last two years for the rent receipts (look for steady on time payments as well as consistent amounts.).

Can always make a large principal payment and recast the loan 

Payments show up on time.

If so, can additional funds be brought to the table to fund the new property's down payment?

The money you spend on your Hawaii trip would be a down payment for a house.

Think about when people lie to you, do you trust them next time not to lie?