There is also a ton of different financing strategies available other than your conventional mortgages.

You will not be able to get a Conventional (Fannie/Freddie) loan with the LLC holding title.

Account Closed a PMC has two options to get liability insurance (tenant slip & fall) protection:1) Get added to owner's policy as Additionally Insured (NOT named insured).2) Setup a master commercial policy and add every property they manage to it and then charge those owners the cost of the policy.Otherwise, a PMC CANNOT get liability coverage on a property they have no ownership interest in.So, nothing wrong with their request.

I am looking into purchasing a second (vacation) home and would love to hear your thought on the pros and cons of going a conventional 30-year second mortgage vs. using a HELOC or Home Equity Loan on my Primary Residence to purchase the second home outright. 

Typically they charge a percentage of the amount saved. 

(It could be rented for more, maybe $3000/mo, but I'm only comfortable charging so much on principle.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

California charges a minimum tax of $800 a year per LLC, and more if you have gross receipts in excess of $250k.

Contrary to what was stated in a previous response, brokers don't all charge points.

Consider looking into FHA or conventional loans with lower down payments to maximize your cash.