You act like you’re sharing a secret with the world when the world already knows about search engine optimization.

Having this bird’s eye view of my income for the next few years, how can/should I be optimizing this situation?

There's < 2 months of seasoning for the purchase, cash into the deal is ~$975k w/o rehab (minimal planned so far - turnkey), purchased the property for 35-40% below assessed value, 825+ FICO, and would optimally like to pull out $975K-$1.15M of equity.Main scenarios we've thought of to accomplish this are: 1) structure sale of property from SMLLC to self and secure 30-year new purchase financing on deal (unsure if legal and tax implications if above initial cost basis)2) delayed financing (LTV restrictions a concern)3) cash out refi (seasoning concerns)4) DSCR (seasoning and rate competitiveness concerns)5) one of the above plus a HELOC, personal loan, etc.?

Once rents are optimized, the combined monthly rent will be around $4,000.

Your dedication to optimizing your assets is commendable, and it's essential to explore options that align with your goals.Each of the options you've outlined presents opportunities to leverage your resources effectively.

Optimize your efficiency and focus on high-value activities.

We have a building that is about 5000 sq ft (4000 first floor, 1000 second floor), we are trying to figure out the most optimal thing to do with it.

My strategy would be to protect the money optimally from the government and from other potential filters and to optimize my time to do what I enjoy doing instead of worrying about real estate ventures. 

Now you can educate more / optimize. 

That information paired with a goal or some factor you are optimizing for, will usually lead to an informed decision for your situation.