This is the same if you made an improvement to your home like finishing a basement or adding in a pool.

What's his home improvement contractors license?

Were there any unexpected challenges when working with Plastiq or Fund & Grow that I should prepare for?

Today we have 540 units in a few states and things are not without challenges. 

Looking to improve my investment skills, I decided to get my residential home inspection license which led to me starting HLC Home Inspections.

Most traditional property managers don’t handle this setup due to challenges like managing tenant disputes, coordinating overlapping move-ins/outs, and the risk of Fair Housing violations when selecting tenants.

It sounds like you navigated the challenges well and gained valuable lessons for your next venture.

Of course I inspect and think of ways to improve guest experience.

You can use that scenario as a learning experience when you may or may not encounter future challenges. 

Add the financing challenges and that you existing structure likely will become rent controlled.