Has anyone ever done an analysis to determine if it is financially beneficial to pay off an LID (Local Improvement District) assessment early? 

As @Eamonn McElroy mentioned, S-corp will be most beneficial once you pass 40-50k. 

Money is made when you buy a house not when you sell it so how is this beneficial?

This may be more beneficial for a OZ fund or a high net worth individual.

Newbie here. I will at sometime in the near future begin real estate investing. I'm currently working in an unrelated field working paycheck to paycheck and not able save any money. I am considering a career change to...

Ultimately my question for you is what is more appealing/beneficial to the value of my rental?

@Preetinder Singh Fun fact: Connecticut and Florida have reciprocity, or mutual recognition, so once you get your license in Connecticut you can just take the state portion of the Florida real estate exam to get your sales associate license here. 

A foreclosure will likely cost $4000 to $5000.If you can mutually agree on a way the tenant/buyer leaves without going to court it should be cheaper and quicker for you even if you need to pay them some to agree to this.

Many title attorneys here also will not clear the title if the deposit and contract are not mutually released.  

I’m Currently looking at a Potential deal in GA and any information prior would be beneficial.