I don’t plan on purchasing this property as I am due to move and be out of the country here soon, but when I get back into the lower 48 I am planning on taking more action on potential deals.

Not sure where you live, but if you can rent a place for $1000 or less, you'd still be $500+ positive each month.

So if your RMD value for the year is $2000, as an example, you need to ensure that a rental property creates at least that much positive cash flow after expenses.  

Problem: Being that it’s a condo, I will be paying a HOA, but if I’m calculating correctly, there will be a decent positive cash flow.Thought Process: The lovely prices of single family or multi-family homes are a little out of reach right now, which is why I’m looking into a condo that I can afford.

But you're right, once you view it rationally like that, it can remove the emotion and put you in a position to learn and grow from it (which is exactly what happened to me here). 

@Thadeous LarkinPerhaps look into refi your current when you can do a new VA, equity and cf position if rented.  

Andre Rembert - you can theoretically wholesale if you get a mls listing under contract for a lot below asking price and you’re buying it as an LLC or in an assignable contract (you sell your position as the buyer).

Should I start with one or both positions?  

Having such a large amount of negative equity and they could call you before that mean letter if you feel positively about their market value that can be more appetizing with a decent offer over their high negative equity.Good luck to you!

Getting good at the math will ensure positive cash flow.As you learn you’ll start to narrow your focus.