You want to crush your job so you keep getting promotions and keep making more money so you have more borrowing power.

(completely passive, some activity, very active). 

I can filter out things like active/pending MLS or recently sold properties.

I also actively invest in real estate.

Do not expect that to be the pref. but total IRR after receiving the promote.2.

I've added him as an account manager in the account so that he can see the activity.

I'd shy away from actively openly sharing the intention to do it beforehand. 

And while it is not the sexiest, maintaining your W2 job and working hard to get promoted and earning more, even if that means changing jobs every few years, is often times a faster approach to create investable income.  

HOA and insurance costs as low as possible.Can you suggest a few good cities in the FL with lower vacancy rates and close to nature/activities?

Our track record of over 36% IRR to our investors is hard to match in this industry or any other (and that includes two recessions, unlike most of the currently active syndicators in our space).