With regard to your "DST" and as with many highly structured tax vehicles that have a potential "self dealing" quality to them, there are a number of potential potholes you can easily step in along the way (e.g., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).

Hi, As a property manager (based in Chicago), I have to say the screening process is paramount, because its the start of your relationship with various prospects.

Additionally for hosts who opt for enhanced screening, the eviction rate is under 2%. 

I learned that it's better to go for quality the first time if you want it to last.Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Buy from a quality builder in a neighborhood which is going to appreciate.  

You should focus on the quality of the agent, not the amount they charge.

Another key aspect of creating generational wealth is investing in high-quality properties.

While you shouldn’t categorize all tenants and it’s the landlords responsibility to properly screen, the tenants who reside in better situated housing and pay higher rents are more financially responsible meaning lower rate of rent loss and will generally take better care of the property which combined will result in less time allocated towards management functions if self-performed or more favorable management fee structures if 3rd party management companies are utilized (which ties back to #1, as well).

The only challenges you haven't mentioned is advertising for roommates, screening them and where to get a lease.

I know you can’t predict this but I try to get quality purchases which helps.