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.

The main house is completed and as far as labor, I spent $40,000 on just labor and that includes everything from full gut demo to finishes.We are talking about a 4BD, 3BTH two story 2400 ft.² home with a bonus room.This was a full gut job, replaced…12 Windows (new construction)2 sliding doorsTook out all carpet throughout.Took out this ugly 2” thick tile from half of the downstairs portion.Removed popcorn throughout the entire houseTook one wall downA little framing workReplaced entry door 80” x 92”Drywall patchingSmooth drywall work50 recessed lightingAll electrical neededAll plumbing neededNew cement walkway instead of one walk to the front door I created two steps with two lights in each step.Install kitchen cabinets, excluding countertopInstall all three vanities3 bathtubs with one being a modern standalone tub in the masterAll tile work (bathroom wall & floor, kitchen backsplash)Installing of all hardware, faucets, showerheads, etcInstalled 8 single panel doors with hardwareAdding self-leveler after tearing out that thick tileNew LVP flooring throughout the entire house except bathrooms,all baseboards, trimsPainting the entire house, painting all the doors, painting the outside trim.Reframing the outside balconyReframing the fireplace to install new linear modern electrical fireplaceand they took care of the two trash bins.I mean, completely redone.The only thing that was not included in the $40,000 is landscaping, counter top cut and install and of course the ADU which I’m currently working on now.So my question for my fellow investors and contractors did I pay too much?

Full paint 2.

I'm not trying to rip into the work and expense you've done, but for not much more per night, I can get something really great with more bedrooms across the street in Championsgate, Windsor or Solara.I'll jump in about the grill too, that's way too much, especially since your title says "Pool & BBQ", but I have to spend extra to get the BBQ part.

If he does move out and has been there for 24 years, my guess is you are going to have quite a few expenses (ie new flooring throughout, paint and possibly updates-countertops, etc) just from normal wear and tear. 

A typical turnover can be a month or 2 of vacancy and $2-10k in make-ready costs (cleaning, paint, flooring, appliances, towel racks, vanities, etc. that gets beat up and broken norma wear and tear).