Someone will lend on the property.I have used 3 different brokers who shopped around for me.

Regarding insurance, i would recommend working with an insurance broker (happy to DM you the one i utilize) and they can shop for the best one for your rental. 

The Short Term Shop operates here and would love to help!

You may have an amazing gift from Uncle Sam.

answer to #4: Speeding things up to do more deals every year, i'd say begin looking into partnering on deals with friends or family who perhaps have yet to purchase a property so they can use an fha 3.5% down or 5% down conventional loan, you gift them a portion of the downpayment for a % of equity in the property.

However after talking to my lender, he said that we would not be able to use my fathers "gift" to purchase an investment property.

The beach community may be attractive even if a mile away depending on the micro location, is it walkable, bike paths, coffee shops, restaurants etc.

Box A is direct lender charges, box B are things the lender is making you get that you cannot shop for (for instance, the appraisal or credit report), and box C is closing costs that you can shop/control- Lenders can move things around between boxes A and B to change the way costs appear.

I also recently found out about Latte and Lease's Out of State Investor Academy's "Cash Flow Coffee" meetup, which I believe can be accessed via her email list or her website: https://www.lattesandleases.com/shop/p/bay-area-meet-up-g9ny...

The further south you go from HWY 160, the longer it takes to get to shopping, jobs, etc.