I may want to do a cost segregation study and look into tax benefits.

Pay an Immobiliarie to do the study.  

Consider a cost segregation study for your rental properties to accelerate depreciation deductions, significantly reducing your taxable income.

And lots of other goodies, which I won't bore you with cause it will sound like self promotion, which isn't my intention here.

I am a senior at the University of Colorado Boulder studying finance and real estate looking to move back to California after graduating in a few weeks.

I study, read, listen to podcasts daily.

I’ve been studying the strategy for awhile but I’m still nervous about doing trying ut. 

My guess is there will be dozens, hundreds, or thousands of case studies to examine a few years down the road to use 20/20 hindsight to evaluate outcomes.On your second question about extending grace vs being tough: that also depends.

I know that in the bigger scheme of things, that's not a lot of studying/researching but I did learn a lot today and looking forward to learn even more. 

Invest based on your goals and resources, make sure you study everything before investing.