If you need more coverage, you can usually increase the liability amount on your current policy.

And they just increased their rental limits to try and keep pace with cash tenants, so if Section 8 is part of your strategy, now is a great time.

Your insurance is going to be highly variable and I wouldn't use what an agent or the seller tells you as the cost of dwelling policies have increased substantially over the past few years due to rising new construction costs. 

Land that you're not personally developing most of the time falls into two categories - either you're speculating that development is coming that way, and will increase the demand for the land, or you're changing the current permissible use of the land in such a way that it will be worth more money now or in the future.

I would caution you against increasing the down payment to make the numbers work.

2) Is the extra LTV on cash-out worth the increase in interest rate and if not, how much LTV would I need to go get the next property?

I believe CA market in general is expected to increase by 4-5% but SF is unique. 

My property tax increases have been 17% for both homes (no Proposition 13 like in CA with our max of 2% increase).  

The shorter the prepayment term has an impact on increasing the rate.4.

After these meetings, the GC often asks the subs to increase their bid.