I am a Painting contractor and can help with any of your needs. 

- Why does it cost more per sq ft to paint a Class A property versus a Class C property?

Painted the entire home.

For example I had my GC purchase paint, countertops, and flooring using his connections who worked at those locations to get a discount.

Nail holes need to be filled where tack strips where, but ripping the staples from the hardwood resulted in several rough spots that need to be sanded down.We have no experience with hardwood refinishing- what are our options to avoiding a full scale hardwood refinish?

Also, love to work out as much as I can in things like running, bicycle, jumping rope, and lifting weights-no ripped or jacked by any means-but thinking in the long term benefit (like in real estate).

Upgrades/repairs include:flooring (tile and carpet, entire house), painting (entire house), complete kitchen renovation with new appliances, cabinets, sink, lightingcomplete bathroom renovationsupgrade/replace ACupgrade/replace existing hot tub  upgrade/replace furniture/bedsupgrade/replace old pier with newadd new kayaks, paddle boards, and bikesI am thinking anything that is removable (furniture, appliances, water toys, bikes, pier, etc) could qualify as an asset for the LLC and thus be used as a tax expense for the LLC.  

Full new paint, new flooring (vinyl plank vs carpet), new cabinets, countertops, fixtures, sinks, tubs, lighting, basic rental grade appliances, etc.

Obviously I am a newbie in the game and I do have that newbie skepticism and always feel like I am being ripped off ( has happened many times before).

In most markets that's closer to "A" room paint with trip charges.