Show me any math that works in reality, and I'll give you 100$. I forewarn you that I am a nominalist, so it would not be an easy belief to shake, as it is supported quite well.
Let's say you have 5 bowls, each with 4 apples.
How many apples do you have?
5*4=20.
Guess what? That works in reality.
1.9999... does not work in reality. You are dismissing 1.999...99923 because it does not work in reality, when 1.999... the series you are claiming = 1.99...999 also does not exist in reality.
To your apple point though, this is an issue many young students struggle with. It is also how many children learn mathematics. Let's talk about it a bit.
So, let us discuss the entirely similar situation: let us put two apples on a table - a sturdy table mind you that would not shake or move the apples or bring in other apples by accident and so on. Now we then put another two apples on the table, and count those now there - we will likely get the result 4. We can perform additional experiments like this, but we are fairly confident here that 'adding' works as we think it does. Yes, the results are consistent, and perhaps even corollary, but this is not the same thing as placing two numbers ones on a table and then two more number ones.
However, if we did the same procedure with sticks, fingers, line and most things this would show us that sums are completely silly. Look at this figure to see 2+2 = 4, which is similar to your argument:
If this is all we need, as you claim, to show that 2 + 2 = 4 and in your case 5 + 5 + 5 +5 = 20, then this is completely valid reasoning:
2 + 2 + 2 = 4.
Source: Remarks on the Foundations of Mathematics; Page 52 MIT Press 198
For similar reasons, your supplied example is not sufficient to show that 2 + 2 = 4 in reality, or that 5 * 4 = 20.
Edit: filling in the dots.