I have a good enough income that I don't NEED to sell it for money right now, and even with a property tax bill close to $15k, I believe that beachside property in Carlsbad is a great asset (it's not like they can just make more of it).

Yes, you can do a cash out refinance on a property owned free & clear!

Your blended rate will be better and you can focus on hammering away at the 2nd mortgage which is the higher interest rate. 

Yes it can be worth it, just don't expect to get rich quick lolMidterm rental has been my strategy and I'll definitely be sticking to it for the next few years.

Anyone know where I can find it?

You can also check meetup.com or search Facebook for real estate investment groups, clubs, or meetings in your area. 

@Maureese Jones - we can look at this one. 

Can you sell your currently live in property to your LLC?

I am in talks with an insurance lawyer now, but how can I ensure to have max payout?

You can advertise no pets which will eliminate most people and just deal with the few that do reach out.