I also do business in Monroe & Old Bridge. -- I will DM you as well! 

does having a long LLC history 10+ years  in business help in any way Just asking dumb questions (Thanks in Advance!!)

Quote from @Yates Harris: Yes, you are overthinking it.Insurance companies are in the business of making money.

We also have an onsite manager who is handling the day-to-day business. 

IMPORTANT:--Guest communications, including setting up your automated messages--Price adjustments (key into seasonal pricing and important events in your area)--Listing description and noting amenities--Guest reviews--Learning from experienced hosts with great reviews (you can do this on many social media sites, including the Facebook group, Short Term Rental, Long Term Wealth)UNIMPORTANT:--Watching your Ring Doorbell camera--Obsessing about minute details that other hosts are freaking out about--Being a control freak about ANYTHING related to this business. 

I need advice…I am buying my first investment property in May and will put it under a new business.

Specific Business License: If I create an LLC specifically for the property management side of things, can I obtain a specific business license for this?

Throughout my life (grade school, college, business), I've always been a big advocate of taking notes and organizing different sources of information into one place, making it all easier to digest.

You get started in the market and get a sense if you even like this business or not. 

I deal with a lot of these people because our houses are mostly new constructions and great for business like this.