Right now in particular, I'm currently fighting with the hot water tank & gas furnace, hoping to find someone who could check those out without me having to contact a major company to come out for a service call and then be upsold into purchasing a new unit.

I wrote a post on how to find comps and calculate ARV that you might find helpful: https://www.biggerpockets.com/blogs/8814/68395-how-to-find-real-estate-comps-and-calculate-after-repair-valueTo answer your major concern, when you get comps that have a large range, there’s usually a reason that you have to dig deeper for. 

Total rent should be $800-900/month.After inspection major issues we found were:-gutters/downs need replaced, drainage run away from home (water in basement)-chimney needs tuck point at minimum, bricks falling off-mold growing in basement (big chunks of white growth along all wood)-cosmetic work about $2k to upper unitSeller wanted $14k, we offered $10k due to the amount of work we need to put in.

I have also gone through various posts and online but I havent been finding the actual numbers gameIs there a specific value calculator like Bob talked about?

Looking online GC liscense seems to be a pretty reasonable process to achieve??

I would hire out the skilled labor, but do the majority myself. 

If you are just going to look online and try to find something that seems to fit the 1% you are likely to be rolling the dice.  

There are many online sites where you can pay$65ish and they will send you a fabricated letter.

All of my files are stored online, I can access them from anywhere.

@Josh ChappellI would say the majority of the time, on 1-4 family properties, this is the case.