Overall, my short-term goal is to have invested in my first property before 2018.

More options give you more chances to win.Yea, you may make a few bucks if you invest it in the meantime by investing in the market, which you'll have to pay capital gains on (short or long term depending on when you buy/sell) or the stock market may take a dive in the next couple of years and your $25k is now $18k, which changes your math for you ultimate goal of a MF house hack.

That may require or a short sale or not depending on their equity which you may not determine easily without that initial discussion.

Nothing wrong with your setup using jobs, it's little more details than I need.For data entry purposes, keep your class codes short, or you will have trouble selecting them in the input screens, which has room to show the first six characters.

My girlfriend and I are investing in short-term rentals.

Joshua, This one has already had an offer accepted contingent upon an inspection and short sale so third party approval required.  

Short of that, I recently heard a tip on one of the BP podcasts...go to Home Depot at 7am and talk to the contractors getting an early start on their work day.

The short-term timeline for the $100-$150k is 1-5 years with intentions to keep that money working.

I would probably provide a short list of minor upgrades that they can choose to do to add perceived value as well.  

You would not even be able to payoff the short term loan used to acquire the property.