A few days ago I visited an off market property in Austin in a well established neighborhood if interested feel free to connect. 

Question 2: Where can I find state or city regulations regarding tree maintenance when the lease is written with gray areas?

Be aware of any local regulations in Emeryville as well.Please make sure your 4plex isn't exempt from AB 1482.

The regulations in Chicago can be quite overwhelming, so I’m looking forward to exploring the opportunities in this area. 

A connection of mine is well established within the energy realm in NH.

So, I’ve developed a list of what financial intermediaries SHOULD and SHOULD NOT do in order to establish a viable, sustainable intermediary business1.

I was looking into the cities regulations and it seems like mid term rentals would work.

Use some for buy and hold (I personally would prefer apartments rather than buying a few single family homes) and some for lending/trust deed investing.In either category, you must know what you are doing, know how to vet the investment, how to vet the sponsor (if investing in a larger fund of some sort), the laws and regulations on the lending side, how to investigate which areas to invest in buy and hold and notes/trust deeds for that matter.So as you have already said several times, lots to think about . . . 

Maintenance and Repairs: Property managers have established relationships with contractors and vendors, ensuring timely and cost-effective maintenance and repairs.

What are you hoping to achieve in establishing an LLC?