This is due to different owner structures, not that each property needs an LLC.

It's like buying a house next to a bus depot.

I'd love to connect and learn about what you're looking for in this next deal! 

Also, take a look at a condo if you really want to be in SB proper, it might be a way to get started, and calculate the insurance and maintenance that an HOA would pay

It was my grandparents' home and when they passed they left it to their 3 children, two of whom (my father included) decided to divest and leave the house with their eldest.

Since your goal is to subsidize retirement, it’s worth considering how much leverage you want to carry as you transition out of your W-2 jobs.

Probably every dialer company has lists they can sell you.I think it is better to call yourself vs using cold callers. 

Be sure to explore all around the forums as well as many of the FREE tools that Bigger Pockets provides.I am on the lending side of things and am always happy to hop on a call to discuss loan options that are out there, even if not offered by my resources.

Anyone have any experience in the area that can speak to rents?

If the HELOC rate gets out of hand, then go to the bank at that time.