A trust transfer allows for smoother estate planning, and if inherited after their passing, the land receives a step-up in basis, reducing future capital gains tax.Each method has pros and cons depending on their estate plans and your long-term goals.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Having trusted resources in market have been helpful in managing our properties and contractors especially when my non-real estate related consulting business is in its busy season.

Investors think in numbers, exit strategies, and long-term plays, while homebuyers think in emotion and monthly payments.What are some of the biggest differences you’ve noticed when working with or transitioning into real estate investing?

My clients are mainly real estate developers, PE funds and individual investors doing syndications and my core skill is in real estate valuation / due diligence across real estate asset classes. 

I'd check local STR FB groups and see if you have a local Real Estate Club.You can offer your services there, maybe for free in exchange for the experience.

Can your real estate investment outperform the long-term returns of your 401(k), net of taxes and penalties if something goes sideways?

The deal was identified by my real estate agent and requires a quick closing.

Quote from @Brandon Morgan: hey guys I am new to real estate and I just got my first rental property this past year and have tenants and things are finally stable now.

This is where it pays to consult with a real estate attorney.