That said, if the borrower is managing multiple projects, they may prefer to keep more of their current reserves to use on other projects rather than saving a few thousand dollars in the long run by paying upfront points.

Compare this to your insurance deductible, which can be high near the coast and, as you mentioned, can be higher during a named storm.One wind claim during a catastrophic event should not cause your insurance premiums to go up, but if you have had multiple claims in the past 5 years, the frequency of your claims could cause an increase.The reason I do not advise you to call the insurance company first is that it will be entered as a claim on your policy, even if you ultimately do not receive any money from the company.I hope this helps. 

You could bump them to $1,800 which saves them $2,400 a year and costs you $2,400 a year.

But you save huge money.

Read books and blog posts here on BiggerPockets and save yourself the money

   Hey guys I'm new to the forum, I just stumbled upon the forum yesterday, I'm 23 years old right now I've been flipping used cars and doing contractor work for the past year and i've saved enough of my profit to purchase my first property, any advice, tips, book recommendations, courses or thread recommendations would be greatly appreciated, I'm in a mode where I have an immense appetite to learn and absorb content.Thanks,           Quin

Meanwhile, save every penny that you have in case a deal falls into your lap.  

If this is successful I would like to move some of my personal savings into multi-family properties as well.

Second, we saved up for a few years and pulled from our HELOC on our new primary residence for the downpayment on a 4-plex. 

Do you have a cash reserve, or have you factored in saving part of monthly rents to build up a reserve?