My concern is being able to get funds for this loan as a new investor.

First and foremost I will also let you know, that I am a licensed attorney in Florida and have designed my program to alleviate some of your "concerns".  

I'm a loan officer with a local mortgage company so if you ever have any financing questions or concerns please reach out, I would love to help you out.

I do not concern myself with the standards and always make my tenant selections based on my own criteria.

Now, a large reason for my career change is hoping for better income, but I haven't seen much discussion on here about needing the income to qualify for both mortgages-- is that a real concern?

If you don't have all of that, stalling a short sale is a myth and urban legend if a bankruptcy filing doesn't accompany it.

As long as you are ok with the cashflow and it fits in your criteria then the fluctuations in price shouldn't be your main concern.

If you would suggest changes/improvements especially where the words "House Gone" are concerned, I would appreciate it!

I'd like to roll the money from that deal into my own apartment deal using a 1031 exchange however I have some concerns and wanted some feedback. 

What is your primary concern?