This problem caught up to me faster than I ever thought it would!

Depends on how much capital you but even with low capital the BRRRR strategy can help you acquire properties faster than house hacking and if you get it right, you can continue doing it over and over! 

It may be worthwhile before your student loans are paid off, as homes generally will provide you tax write-offs, and you may be able to pay off your student loans even faster this way.

But I'm thinking the profit from STRs can be used towards your second home much faster.

As far as scaling goes, on paper a duplex would be faster because of the cashflow.

Combine that with living on as little as possible, and you will find that you can build yourself out of needing that W2 much faster.

It's like the diet and exercise plan for losing weight....it takes time and consistent effort. 

Prices will likely continue to grow faster in the affordable segment of the market for at least the next few years given this lack of supply.

No one likes lugging in window units, plus window units are hard on the home (weight on window, poor sealing, extra load on a single outlet that may have not been designed for that load, etc.).

Or should I buy a smaller condo (I can afford the large one, but I will be saving roughly 4-8K/year ONLY).The small condos around the area are usually around 900-1000sqft and they cost roughly 320-400K.I know single-family houses appreciate faster than condos.