I am a new by and BiggerPockets was recommended to me by the Carolina REI Association.  

My point is I expect rents to rise a lot more than the 3% to 5% you are considering due to the increased cost of RE, the newly identified risks associated with providing residential housing, the high CPI and associated wage increases, etc.I suspect if you raised the rent only 3% to 5%, your tenant may feel fortunate.  

I would like to hear some of the pros & cons associated with this strategy and how successful or unsuccessful this route has been from anyone who has done this.

You may have wanted to go to a private college and not work while going to school, but if the degree didn't get you a high paying job, you made a mistake.

Ideally, I go through as an analyst, then associate, manager, etc.

I've got to say it pees me off to some degree because I'm considering list my place next spring and spent about a year and a half getting the 500 SF home addition permitted not to mention $12,000 in permit fees and feel the sale of that place will reduce the comps to some degree.Question: Have you agents or buyers noticed this shift in your area?

I am working in a clause in the rental agreement that the tenant will be responsible for any fees associated with breaking of the rules.

when your tenants are covering all the debt expenses associated with the properties.  

Besides you get total access to the library of podcasts.It’s might even be a tax write off as a professional association, professional service, or something needed for you property.

(Most if not nearly all hoa associations don’t allow it in SE Florida due to spring breakers) Hope that helps a bit !