You have decades ahead of you to screw up, recover, and try it again. 

Know ahead of time where you want to invest and do what you can to know which real estate agents, attorneys, contractors and property management companies are in those areas so you're not left scrambling for contacts when an opportunity presents itself.

I'm thinking if we can encourage the current tenant to vacate early, we can get a head start on repairs/updates and have it tenant-ready sooner.

All of this has pushed months supply to a new low of 1.7 months. 6 months is considered a neutral stance.

Sounds like you are really ahead of the game if you purchased your home in 2010.

I just got an estimate on a refi and it looks like it would save me $148, but it would push my loan amount to $174K and back to 30 years.  

That gain will likely push into the highest tax bracket and a large increase there and/or less favorable capital gains treatment could be a big stinger.5.

I would say if you know the area well enough and/or have a good Realtor (happy to put you in touch with someone) to help you find a good property then go ahead and buy something now.

@Marcus Auerbach I push back on the premise that the city is fully built out. 

Maybe you’re way ahead in that than me, but I believe we need to work on ourselves first before anything else.