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.   

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

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. 

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.

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

A thermal camera inspection would give better idea if its because of cold air getting in or the room does not have enough hvac / heat source

Hopefully after our conversation, you have a better feel for what to expect.  

Btw, I’ve found that these types transactions actually work better when used to purchase/sell COMMERCIAL property. 2.

Now I'm on the Panda Planner and actually like it better. 

Sometimes an $800k 4-unit could be a better return than a $300k 2-unit...or visa versa.