Re: Just beginning to shop around... would love feedback/ideas...
K, just checked. You're looking at 5 miles from Jack London Square to San Leandro bay. Two miles of that, however, is a bottle neck.
So, if you did something like that, you'd want to leave Jack London square towards San Leandro bay as the tide is coming in, and leave San Leandro bay to JLS as the tide is going out. Though, if worse came to worse, there are private docks you can prolly "temporarily" hang out on, if you get in a bind. Also, staying at the water's edge, as opposed to the center of the channel may allow you to still paddle "up-current" so to speak. That time I got stuck in the current in my inflatable, there were a couple of SUP'ers who seemed to be doing okay.
That being said, it sounds like you are interested in camping, etcetera. Which you would not find in the estuary, as that is pretty much sandwiched between two cities and the airport. Am not sure there are places to camp in Sausalito, either.
In fact, from a camping pov, I expect Tahoe has more places that are conducive to camping via SUP/canoe. But that is just a guess.