Are there any major flaws with this plan, other than tying up a significant amount of capital on the first property?

I had accounted for this in my business plan, so no surprises there.

Some of the residential agents may not know or understand your game plan. 

I plan to convert my Surf City house into a long term rental soon (long term since my HOA currently does not allow STRs).I am an active duty Marine and have been in for almost 10 years. 

I currently have a construction management intership lined up for me during the summer but after that I plan on really taking on this real estate adventure.I plan on house hacking my first property, any advice ? 

However I believe you can do a no fault eviction if you plan to move into that unit.

The advisor is saying that I have a lot of debt and wants me to focus on paying off some other properties with the next 10 years, I plan on retiring at 65.  

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.

For planning, i've found the following to be decent planning factors:  10% property management fees, 10% potential repair and maintenance expenses, plus any excise taxes your area imposes and condo/association fees. 

We have all of our plans and have begun applying for permits (though that is taking much longer than expected due to Ian backup).