Then boil that down to a 1 year goal and then down to a four 90 day sprints or quarters of action.

These are mutually exclusive actions.

It’s time consuming and frustrating but that’s the nature of landlording I suppose 

In the end, I feel like people just try to justify to themselves why they won't take any action to better their position.

You just need to run the scenario through your head and figure out what would the actions/reactions be. 

I am not trying to profit off this, but my time is valuable (~1hr of work+travel) and all actions have consequences  - I want the tenant to understand this.

For non-vanilla non-ho-hum non-SFR properties where you need the appraisal report turned relatively fast, bids are sometimes starting at $1000 a pop, please take a number and get in line, or exit to your left if you would rather not transact (actually, consumer-driven bidding wars are not common, most common is 2 or 3 appraisers name a price/turntime combination, and you can either pick one, or not transact).If the listing agent does not sell a lot of homes, they may be unaware of this.

LIEN AUS ORIG TERM REM TERM Loan Age Orig Rate RATE Current Payment PITI Has Escrow Acct Current FICO FICO DATE Orig FICO ORIG LTV ORIG CLTV CURR LTV FE DTI BE DTI OCC TYPE PROP TYPE # UNITS LOAN PURP Refi Type DOC TYPE QM FLAG Modification Flag Last Modification Date Channel APPRAISAL / BPO / AVM APPRAISAL / BPO / AVM DATE SALES PRICE ORIGINATION DATE FIRST PAY DATE PAID THRU DATE NEXT PAY DATE MATURITY DATE First Rate Change Date ARM INDEX ARM MARGIN First Period Change First Rate Adj Cap Subsequent Rate Cap Life Cap Floor Rate MI FLAG MI COVERAGE % MI PROVIDER LOAN STATUS BK Chapter BK Filing Date BK Post Petition Due Date Foreclosure Date Referred Foreclosure First Legal Action Foreclosure Judgment Entered Date Foreclosure Scheduled Foreclosure Sale Date PAY STRING Days Delinquent Payments Latest Month Payments Last 3 Months Payments Last 6 Months Payments Last 12 Months Notes COVID Inquiry Date COVID Inquiry Description Forbearance Flag Forbearance Agreement Date Forbearance Non-Pay Start Date Forbearance Non-Pay End Date COVID Opt Out Request Date

If you run background on them and end up rejecting them, you'll have to send them an Adverse Action notice (FCRA requirement). 

Ive been doing a lot of research in the past 2 weeks about real estate investing and am very motivated to take the jump from just learning to action in the near future.