Love the honesty on the emotional attachment aspect.

You're an economics major so I hope you are seeing the signs that the economy is in a downturn in all aspects including Real Estate.

No different than a long term rental in that aspect. 

If it's a bigger job and I am paying the tenant, I spell out exactly what I will pay  with a clearly defined maximum.

Looking to double the STR side this year, but interested in learning about all aspects of Real Estate. 

Going from home, to not dorming at college, to still living at home (all in the middle of COVID), to then being a home-owner, seems like I am missing out on the social aspect of living arrangements, if that makes sense.  

If your goal is a dependable passive income that will get you off and keep you off the daily worker treadmill, you partially defined the location requirements.A dependable passive income is -Reliable - You continuously receive income in good and bad economic times.Inflation Compensating - Your rental income grows faster than inflation, compensating for rising prices.Persistent – The income continues for a long time; you and your spouse will not outlive the income.2.

I definitely need to work on the local market knowledge aspect 

Clearly define what the minimum and maximums are for your downpayment, purchase price, cashflow, NOI, CapRate, asset class, total number of units per building, etcThis will give you clarity as you scrub deals.

Start by defining your sample groups.