@Natasha Jansen Good luck on the development it's definitely a nice added bonus that you already had the land.

For example:Generate just a few more clients per year to make up the costGenerate leads and start a team, splitting commission with those agents that don't know how or don't want to do lead gen (and as an added bonus, you can get others to cover the cost of the ads)Become a top producer and get your entire cap backGet your cap back for growing the company by just a just a handful agentsUse a national referral network to either get a few more clients or get a few more referral checks by finding agents for clients out of your marketJust some ideas for ya. 

Our manager is amazing, keeps our rental booked year round, and I never have to do a thing.

An added bonus it sounds like California I would only need to pay franchise taxes for the holding LLC even if I have numerous additional LLCs.

Lets call that the :( side.2) And there is the happy side... passive income (syndications, passive partnerships ie medical/dentist offices) and passive losses (depreciation, bonus depreciation via cost segregations common in syndications).

Due to some personal decisions I bought a new home in round rock, about 7 miles further north of my current place and I'm moving there in a couple of months.I was initially planning on selling my Pville home right after the move but now I'm thinking I may keep it for a few years, perhaps for another 5 years or so while the original builder warranty is still active, and keep it as a rental.

If they are located in the Chicagoland area, that would be an added bonus but possessing working knowledge and expertise are the most important attributes. 

Well I'm 100% dead set on SFR (3bd 2 ba) primarily in the Round Rock/Georgetown/Pflugerville region.

Some of them are financially capable of paying but decide to use their stimulus check and bonus unemployment to buy a brand new car (I had one of these). 

Due to some personal decisions I bought a new home in round rock at the begining of 2020 about 7 miles further north of my current place and I'm moving there in a couple of months.I was initially planning on selling my Pville home right after the move but now I'm thinking I may keep it for a few years, perhaps for another 5 years or so while the original builder warranty is still active, and keep it as a rental.