Mortgage balance is the same. i think his payment is around 1200/ mo, and rent in the area might go for 1500/ mo.

Im not sure how your local market is, but if it was me I would find a balance of investing and living.  

@Annelyse Finley it seems like there is some good advice about looking at what other investment opportunities could be had if you weren't tied up in this condo.Two other things I would note: a) look at the tax implications, for example are you going to hit the limit for your primary residence gain on sale exclusion, and b) assuming you are not short on cash, I don't think the $1,000 cash outflow is the relevant figure to consider, I'd subtract out the average amount being paid towards the mortgage principal balance each month.

and any tips/experience on maintaining a great work/life balance while running a prop management business?

It's all about how you want to do your bookkeeping,, carry over the balance every month, and continue to send past due balance notes on the outstanding late rent fee or write it off.  

I would like to discuss the balance of being an agent-investor, or investor-agent (whichever way you identify).  

At the end of 20 years you’ll have appreciated to $530,660 and the loan balance decreased to $103,142.

Why on earth would you assume the mtg balance is the sales price?

You take the place of the existing borrower and "take over" their mortgage at the current balance, rate, and terms, and the existing borrower is relieved of all responsibility. 

IF you have had the card for a while, ask if they can increase your credit limit than do a balance transfer.