CAUTION:  Be careful of syndicators who use absolute terms like Always or Never or Inflation Protection, etc. as these are fluff. 

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

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 ? 

So, I think they should be considered carefully before doing.

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

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.  

You have to be careful on taking this decision.Problems to solve:- Reduce vacancy.- Improve in property management.Then you can think on expanding your portfolio.A good investor would need to have the hands on the ground to make sure that they understand what is going on.

The owner really likes one of the tenants but doesn't care about the other.

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.