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.

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. 

Honestly, it's from studying hard and actually implementing much of the advice of gurus like Dave Ramsey and Robert Kiyosaki, and people here on Bigger Pockets and other financial podcasts and books. 

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.

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

In my particular case, it was recommended I get a WY Statutory Trust for each property and then have a separate CA management LLC for our STR's that would rent from these Trusts in lease agreement/rental arbitrage situation.I usually just trust the professionals, as I know you've studied and practiced this for many years, and I'm just entering the space.