My day job is in IT but now that I am facing the need to either invest in more schooling to advance in my current field or change fields, I am determined to get away from the uncertainty of relying on others for my employment and be my own boss. 

You picked the wrong forum.

The tools are awesome but I'm struggling to pull comps to determine ARV. 

Think long and hard if you want to apply for a variance (zoning determination or code interpretation) just for you to bring in a new tenant and make more money.

As long as they are patient, licensed and willing to help you (and they should since there is a possible commission at the end of this rainbow).I would suggest starting with one of the national realtor sites (zillow, redfin, realtor.com, etc), search for multi-family properties all over your area, pick one (anyone that looks interesting) and call the agent to get details. 

I have a quick question that I would like to pick everyone’s brain about.

First determine what you could sell it for and calculate the net proceeds.

Over 90% of the time people will pick it up.

(slightly more expensive)- Should I get replacement cost coverage since the market has picked up so much for a new build?

If I am utilizing a LOC against an investment portfolio @ 4.25% Interest with no term, and financing the entire deal, would my Cash on Cash be determined by dividing my annual revenue by what I paid annually to carry that LOC debt?