Excellent response, @Dave Foster, that's a great strategy! USE that tax code!
And @Jason Clark, you've got an enviable Problem... Myself, I'd choose montana any day, but you have to love winter as much as summer for that. Also I'm not crazy about humidity...
As far as investments go, I'm kind of perverse when it comes to using leverage on everything. My favorite is anything like the BRRRR strategy where you use your cash to get the property, then do what it takes to refinance it so that you pull out all of your cash. Then, as long as it cash flows, your return is INFINITE, since you have none of your own money left in the deal. You take that cash and do it again, and you're realizing excellent 'velocity' on your money. And you still control all of your money!
I know the temptation to use all cash so you see really nice dividends every month, but you're only using a tiny percentage of the potential of your money. From where you're sitting, you have the potential to have an empire using other people's money.
When we start talking PM, in my humble opinion, that's a terrible idea!! So sorry all you awesome PM's out there who are happy as a PM... to me, that's the worst part of RE investing, and the first thing I put in my pro forma for properties is making sure I can FIND a good PM and of course that the property will support paying one well. Because the only way you can make any money at property management, is by having a boatload (like 200 plus) properties. (please tell me I'm full of BS, all you PM's, if this is not true) That's the only way you can scale it up to hire all the people you need for Leasing, bookkeeping, etc, and to be able to have an after hours service to handle emergencies, so you can ride your harley on the weekends and sleep at night without being interrupted.
Instead of taking all the time and headache of building a PM business, I'd use your money to find and buy and sell investment properties. It's SO much more fun and pays better too, I'd say, if you do it right. It does take a little time (though not nearly as much as building a profitable PM company) to get good at it, but finding someone you like with great experience to help you should not be a problem. Partner with them and learn the ropes... using a little caution, and spending time researching the markets you want to buy in, you can see some fantastic returns, and then it's amazing how fast your portfolio can exponentially grow. I invest for cash flow, but I love the sneaky creep of bonus appreciation... as you've seen, if you pick your market well (as you did in SF), you might see appreciation (on single family up to 4 family) of a minimum 5% and sometimes 10% or better on the full value of your property... that means that if you have a million dollars worth of rental property, which you only have maybe $250k invested in, you might see $50k to $100k in growth per year ON TOP of all the cash flow and tax savings and mortgage paydown. That's between 20% and 40% COMPLETELY passive income on your $250k investment. I love that.
Most people say don't buy for appreciation, but I've seen sharp folks with deep pockets buy in hot markets with negative cash flow because they have enough money to gamble and still survive if they lose, because they are banking on that appreciation. And they win big in a couple years in the right markets. Or not!
Anyway, good luck and think other people's money!