The winter months, it's pretty much empty but the summer months makes up for it. 

I told her I'll keep the rent at $800 and she'll have 3 months to relocate.

But you do have the room sharing.. in Cupertino were you have a huge Asian population I know folks that will put two computer kids in each room for 4 bed house 8 techies and each paying 1k to 1500 a month.. can just about make it work since the houses are 2 mil. 

On property number one, I would cash flow $750 a month after mortgage, taxes, and insurance if I also rent out the unit I live in.

You might find it useful to attend a meetup or two just to learn how other folks got their start into the industry :) I host a small/intimate meetup once a month in LIC, check it out here: https://www.biggerpockets.com/forums/521/topics/1214850-meet...

You will likely achieve a better return than adding an ADU.Good luck My partner is building an ADU for under 200k in 3 months.

Is your total monthly rent around $12k?

Especially if it’s less than $1,000/months per property.

I'm currently grossing around $2,900 in rent per month.

I heard that PropStream updates this data on a weekly to monthly basis, whereas PropertyRadar updates the data daily, providing fresher leads.