In regards to the problem of specifically finding a deal, I developed a platform with the aim of easing the property-finding process for single family properties on the MLS.

We manage over 650 doors and ShowMojo has been great in streamlining that process and scheduling showings in pre-defined time blocks.

Chicago has far better investment opportunities and it makes sense to keep building on the processes that work, if they are working...

They make sure the tenant doesn't fall behind, and if they do, they start the process of removing the tenant.

Markets closer to where you live tend to be easier to get started with as you might be able to learn the processes of managing a short term rental.

Eviction rates are less than 1% and process is very quick.

Though, this process will be the same for the other state (if you created a CA LLC you may need to register it as a foreign LLC in the state in which you are doing business/holding property).

Our screening process tends to keep riff raff out, but like any real estate deal we see the occasional problem child and deal with them swiftly before they upset the order of the home.  

Tax Benefits: Florida has no state income tax, making it an attractive location for investors seeking to minimize tax burdens.5.

Just spend the next 6 months browsing these forums, listening to the podcasts, reading a few books.Then start connecting with local realtors, general contractors, and developers.Post any specific questions you have about the process here in the forums and you'll get answers within a few hours.