For Buy and Hold investors, there's a myriad of questions that are clearly outlined in the Federal Fair Housing regulations -- IMO, this is a first read primer for the B&H REI.

A year lease, which is typically preferred, actually works against him in the case of bad tenants and strict Californian landlording laws.What are your thoughts?

Qualified Intermediaries are a relatively recent phenomena (mid 80s ish when the tremors of the starker case finally worked through the system) brought about by the regulations changes after Starker v commissioner.  

As a LL, you will run into this from time to time and it's a real pain, but if you fail to follow the regulations, the tenant can come back and sue you for the value + putative.

Do I sufficiently school up in the Chicago market and IL regulations and build a bit of a network here to start off, with the ease of seeing many properties first hand?

These are offerings under Regulation A+, which allow raising up to $50M in a "mini IPO".

I think you'll be hard pressed to find a city or town in Florida that regulates against a weekly rental,  but you will find a lot of HOAs that are against it, so I would look at your most popular places, check the local regulations, then when you start looking for property check the Association rules. 

You never know unless you ask.Once your loan is approved, it is very important that you maintain a strict timeline, stick to your budget, make timely payments, and payoff the loan as agreed.

What do you look for outside of strictly financials? 

They should call it "renter control" since the landlord loses control of the property with the rent control regulations.