I am working on final details for our first flip and have been trying to find a good template for subcontractors we have hired and cannot find anything on bigger pockets or google.

So I am at a loss and would really appreciate any advice. 

I think you get a lot of information and can ask all the questions you need in the Bigger Pockets bootcamp along with Avery's book! 

I recently bought my first investment property with a conventional loan, but the lack of W2s and living overseas made it a bigger hassle.

It’s a huge renting point and can help you get bigger rents.

One thing to remember when you are getting into RE investing is to have your team of people or as Brandon Turner from the Bigger Pockets Podcast calls it your CORE 41.

I'm joining Bigger Pockets to try to connect with people who can teach me and encourage me.

It does not seem as important when you get started with one or two, but the issue keeps getting bigger

The agent says that conservatively I could bump it up to $1600-1800, with it being at $1400 would you say I should try to increase it to $1500 for next year and steadily increase it from there or make the bigger jump straight to $1600+ and risk losing the tenant?

It only happened once, so you have no evidence that this is anything but an honest mistake that's been corrected.The bigger concern is the 583 credit score, because it shows a pattern of financial mismanagement.