Right now we're replacing windows and installing new siding, inside is gutted.

So yes if you manage yourself they can make a bit more but you are also laying for utilities, furnishings and any time a sofa is broken or a TV is stolen you have to replace it and is a sunk cost. 

It has a recent roof replacement, septic inspected and good, HVAC looks new and kept up, and though the foundation hasn't been looked at by anyone professionally it doesn't appear to be cracked etc.

The "workmanship" that we're seeing, across the board, is nothing short of disgraceful - paint hiding rotten siding, vinyl flooring over rotten sub-floors, "new" shingle roofs over 2 old roofs where the structure can't support it, load-bearing walls removed with no structural replacement, even a swimming pool that was buried.  

I am planning to replace the carpets with luxury vinyl flooring in both the living space shown in the picture and the bedroom.

If you tried raising rents, and your tenant ultimately leaves, are you able to find a replacement tenant at market rent the first day it is listed or would it take a couple months to rent the unit.5) What was the previous landlords history of raising rents, and what is the tenant used to?

You will patch a lot of walls, replace a lot of flooring and appliances.

$40k into the deal with down payment, closing costs, replacing furnaces/adding AC, and a couple misc. items.

The current windows are super old and need to be replaced, I just don't know where to start.

The new rental has a modern kitchen, new appliances, LVP flooring, new central air, LED lighting, new window, paint, texture, etc.