I am a software engineer so I prioritize partnering with the right team to execute every steps of investing.

I plan to never pay tax on the appreciation with the current tax rules (1031, die with step up basis, etc).Best wishesYou are way off topic.

He's seen me grow to four units (3 properties) and I'm thinking, there's gotta be a guide or book that would help him just follow step-by-step how to rent out his existing property and buy a new one.

The easiest solution to combine your two Stessa accounts would be for you to add the email address you have associated with BiggerPockets as a collaborator to your already active Stessa account.Then log in with your BiggerPockets credentials (as that collaborator) and it should upgrade your Stessa account.Here are some easy steps to follow: https://support.stessa.com/en/articles/2105533-the-power-of-portfolio-collaboratorsIf this does not work, please message [email protected] and we can work with Stessa directly to get you set up.

I have a lot of things in store and am looking forward to another year of growth and getting one step closer to my goals. 

Are there specific steps or systems you follow to ensure it’s done correctly?

This has been one of our goals since starting the Academy: to help our clients take that next step into purchasing investment real estate in an effort to create financial independence & generational wealth through cash flow, appreciation, and equity.

Are next steps is looking at our first market landscape to get our 1st deal for 2025.

As someone that over analyzes things as well, I’d suggest you step back and think about what your goals are in order to help determine what path to take.I like JD’s suggestion about reinvesting in your business.

What is a good first step?