I'd be willing to bet buying an index fund would have a better return without any of the headaches. 

Quote from @Kody Smith: I am New-ish to Bigger Pockets, and would love to connect with the community here.The idea: move from single family homes into commercial real estate... specifically multi family.The Goal: generate $20k/mo in cash flowI'm currently in silicon valley (san jose)... would love to find something profitable here, but it looks like there are better opportunities elsewhere.I am open to investing in markets across the US.

My cost to Airbnb is better than VRBO and the same as direct (I pay a 3% merchant fee).  

If not then probably better to just continue paying for it yourself, unless you want to speed up the process and you are constrained by cash.Your decision to refinance is going to be contingent on what your long term plans are.

I believe you had a much better-than-average result here.

I could feasibly pursue multiple deals and if I find one in an area I’d like to live once I move back to the US, I would like the option of renting it out while still living abroad but being able to move in and refi to a better deal with an owner-occupier loan.   

If you think the money will come you quick in anything you do you’re better off just dreaming about what you want and saving your money and work for someone else to make their dream come true.

I want to develop my sales skills to negotiate better deals.

You are comparing your units to other units like yours, however, you may want to consider what makes your unit better.

If you can get a better deal on the home due to age its a fine and if you need financing banks do not judge year built.