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The issues is that the standard errors comes from

$$\hat\sigma^2 (X^\top X)^{-1}$$

where $\hat\sigma^2$ is the unbaised estimator and not the MLE. See summary.lm

summary.lm
#R ...
#R    rdf <- z$df.residual 
#R    ... 
#R    if (is.null(w)) {
#R         mss <- if (attr(z$terms, "intercept")) 
#R             sum((f - mean(f))^2)
#R         else sum(f^2)
#R         rss <- sum(r^2)
#R    }
#R    ...
#R    resvar <- rss/rdf
#R    R <- chol2inv(Qr$qr[p1, p1, drop = FALSE])
#R    se <- sqrt(diag(R) * resvar)
#R    ...

This is the observed Fisher information for $(\beta_0, \beta_1)$ conditional on $\hat\sigma^2$. Now the observed Fisher information you compute is for the triplet $(\beta_0, \beta_1, \sigma)$. Thus, I gather the standard errors should differ by factor $\sqrt{n/(n-3 + 1)}$ or something similar. This seems to be the case

set.seed(1)
n = 4 # very small sample size !
b0 <- 5
b1 <- 2
sigma <- 5
x <- runif(n, 1, 100)
y =  b0 + b1*x + rnorm(n, 0, sigma) 

negLL <- function(beta, y, x) {
  b0 <- beta[1]
  b1 <- beta[2]
  sigma <- beta[3]
  yhat <- b0 + b1*x
  return(-sum(dnorm(y, yhat, sigma, log = TRUE)))
}

res <- optim(c(0, 0, 1), negLL, y = y, x = x, hessian=TRUE)
estimates <- res$par     # Parameters estimates
(se <- sqrt(diag(solve(res$hessian))))
#R [1] 5.690 0.097 1.653
k <- 3
se * sqrt(n / (n-k+1))
#R [1] 8.047 0.137 2.338