@Kevin LeAt some point it becomes a personal choice in terms of which area works best for you (SF/South/East Bay/Peninsula) etc.

REebroker is likely your best choice. 

I see the lines between extended stay rentals ("LONG" short term rentals) blurring with traditional rentals.

It Is an option on owner occupied loans where they Give you a choice of 3,5,10,15 or 20% down. 

That's not guaranteed, but it is the choice I'd make based on market conditions as I see them.

Pissed off you have no choice but to pay for 2/3 of the cost.A month later, this Frankenstein'd 17 yr old machine dies out again and the insurance company wants another $99 deposit to come take a look at it a second time.  

With stocks you don't have the choice of buying a nonperforming asset.

@Reyna LopezNo, you won't qualify for traditional conventional financing if you switch from W2 to 1099 (although some alternative lenders have embraced the new CFPB guidelines that don't require income verification).Your best bet, if you are making the money you hope, is to get an asset based DSCR loan.  

I'm a college student and therefore don't qualify for any traditional financing(which I believe eliminates the FHA loan program).

Its tough but generally traditional financing will go off the past 3 years of your tax returns.