Hi Jim,
your complaint is perfectly valid, and I'm well aware we're missing a lot, not just relative to R or statsmodels, but to the old ModelFit as well.
The good news is that most of what you're asking for is already on the roadmap for 15.1. Given the interest (which I'm genuinely happy about), let me elaborate a bit.
And you're right about the documentation: the inference and goodness-of-fit machinery is real but buried behind a one-line mention of "Report". That's on us to fix.
CriterionFunction
I see exactly where you're coming from, and we're going to explain this far better as we flesh the system out. We're trying to walk a fine line between the ML and statistics worlds, so it's going to be a little bumpy at the start.
The key idea is that two things often get conflated. One is the objective the optimizer minimizes when fitting a single model — for most of our models that's the negative log-likelihood, i.e. maximum likelihood. The other is the criterion used to choose among competing candidate models (different hyperparameters, different model classes). That second job is what CriterionFunction controls. The plain is for it to be an in-sample measure like RSquared or AIC, or a cross-validation loss that estimates out-of-sample performance (what you currently see).
So when you see CrossEntropy under CriterionFunction, that's the held-out loss used for selection, not the fitting objective — even though, as you note, it's the same log-likelihood the statistician already knows by name. Point taken on the naming; making MaximumLikelihood (and other familiar statistical names) recognized options is exactly the kind of thing I want to settle when I streamline this in 15.1, alongside a larger built-in selection and support for custom functions.
Inference and diagnostics
We plan to drop the internal bridge to FittedModel entirely and compute every property natively in the new framework. That transition is nearly done, so I don't see a blocker.
As a teaser, here are prediction error bands at several confidence levels for linear, nonlinear, k-NN and decision tree models:

This is currently exposed as a "runtime" property, model[input, "DataAround"]. You can also ask for the full predictive distribution and make some nice plots:

Feature parity
Bringing back the remaining FittedModel capabilities:
- weights
- support for
Around
- categorical data via one-hot encoding
- the missing options
New models
Here the sky is the limit, but at a minimum I want:
- GLM (with a new multinomial link, and likely more)
- GAM
- mixed models
- GAMM
Mixed models in particular are squarely aimed at what you describe — specifying an explicit error structure with more than one error term.
All of this is still pending review, so please treat it as a rough direction rather than a commitment.
Let me close by saying I really appreciate the time and effort you put into this feedback. The framework is very much a work in progress, and comments like yours are exactly what we want!