I understand I'd take a pay cut being an agent for the first few years, but in exchange, I'd be learning about the market and building a network as I move towards Commercial multifamily.

I understand about So Cal.

It’s also helpful to connect with investor-friendly agents and lenders who understand your goals.Good luck!

I understand I can increase liability in each individual landlord policy, but one single umbrella policy is much more cost effective when I have multiple properties.

Just remember that wholesaling is much tougher than all the gurus make it seem to be, but not impossible at all if you create the right systems and understand, when you are new, that you are solving problems, not throwing cash.

The condo is located right near a hospital and McCormick place so we aren't do worried about it, but still a little annoying.From my understanding, the best place to do mid-term rental stuff is on www.furnishedfinder.com

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). 

On the other hand, when you design strategically for a specific type of guest, they’ll not only pay your desired rate but also return and recommend your property.I go deeper into this on BiggerPockets Episode 933, but I completely understand if not everyone finds this info relevant.

Someone who is getting the DOS called is doing things wrong.The guy on YouTube doesn't understand what he is doing.

Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.