Because there have been such significant gains in the markets this year (unless you are a bond investor😬) fund/asset managers and stock traders will likely do some portfolio rebalancing in January, selling winners, and locking in tremendous 2024 gains.

Have yourself own an interest in the LLC, and have another entity you control own an interest and be the manager.  

I manage around 400 rentals and probably terminate a couple dozen every year for lease violations.

Jeff and I lend our own money and at least for me I do have some investors that I manage their funds along with my own.

Why Staying Informed is CrucialRegulations govern every aspect of rental property management, from tenant screening to eviction procedures.

I would also urge you to make sure you fully understand how they operate , A-Z (from how they make their profit to how many doors they are managing). 

Also note that my company will possibly either cover closing costs if we sell or provide property management for two years if we rent.

Do you recommend making relationship with property management companies?

With a natural in and use owner occupied housing, you could likely end up with 1-2 houses a year (each in a new city).The other option is when your baseball career is over, you will most likely end up back in your home town, so you could start the brrrr process there with maybe your parents checking in on the work the contractors and property managers are doing.Best of luck.

@Gary Abrams A cloud based solution would work really well in your scenario of having other family logging in and helping with management.