IBank is not easy either

I assume you are a software programmer because you are in Silicon Valley :-)

To get into IBank, there are too possible places, 1) Hedge funds in San Francisco, that I am not familiar, I am not sure how well they pay people. 2) You need to come to NYC or Greenwich, Connecticut, the so called Finance Valley. Nowhere else can you may more money than NYC/Greenwich, not in Silicon Valley (unless you are working Google, or next Google). Relocation to NYC is hard.

There are other consideration. Although you can make more in NYC than in Bay area, you may probably make 200K+ total comp after you earn at least 2 years experience, but initially, you may not. Nobody is gonna offer you 200K just because you can code C++, you need to know Fixed Income, FX, Commodity or Prop Trading.

Transferring to Finance is one way to increase cash flow, but sacrifice is often great too. In NYC, the work load is so high you basically have to sell your soul to the Banks, 12-15 hours a day is common. How would you get extra time to manage properties. Caring for family could be at risk too.

Your tough nut to crack also comes from Bay area's high home price, but low rental income, balanced cash flow is very hard. See, with the same cash I can buy 2 or 3 townhouses, but in Bay area I can only buy 1. This situation is hurting the LEVERAGE equation. It limits your growth. How you solve that problem, I don't know, it's hard, it may not be solvable unless you relocate to low-cost area. Let's look at Donald Trump, he didnot make all his money from NYC although this is where his home is. He has his investment team spread money across the nation, even across the world to stretch the power of LEVERAGE. Donald has lots of investment in low cost areas like Las Vegas, Phoenix and Dallas, TX. If he was confined to NYC, he won't be as rich as he is today. Trying to extend leverage in high price region is impossible. The cash requirement is forbiddenly high...