ASP.NET MVC: Custom Validation by DataAnnotation

You could write a custom validation attribute:

public class CombinedMinLengthAttribute: ValidationAttribute
{
    public CombinedMinLengthAttribute(int minLength, params string[] propertyNames)
    {
        this.PropertyNames = propertyNames;
        this.MinLength = minLength;
    }

    public string[] PropertyNames { get; private set; }
    public int MinLength { get; private set; }

    protected override ValidationResult IsValid(object value, ValidationContext validationContext)
    {
        var properties = this.PropertyNames.Select(validationContext.ObjectType.GetProperty);
        var values = properties.Select(p => p.GetValue(validationContext.ObjectInstance, null)).OfType<string>();
        var totalLength = values.Sum(x => x.Length) + Convert.ToString(value).Length;
        if (totalLength < this.MinLength)
        {
            return new ValidationResult(this.FormatErrorMessage(validationContext.DisplayName));
        }
        return null;
    }
}

and then you might have a view model and decorate one of its properties with it:

public class MyViewModel
{
    [CombinedMinLength(20, "Bar", "Baz", ErrorMessage = "The combined minimum length of the Foo, Bar and Baz properties should be longer than 20")]
    public string Foo { get; set; }
    public string Bar { get; set; }
    public string Baz { get; set; }
}

Self validated model

Your model should implement an interface IValidatableObject. Put your validation code in Validate method:

public class MyModel : IValidatableObject
{
    public string Title { get; set; }
    public string Description { get; set; }

    public IEnumerable<ValidationResult> Validate(ValidationContext validationContext)
    {
        if (Title == null)
            yield return new ValidationResult("*", new [] { nameof(Title) });

        if (Description == null)
            yield return new ValidationResult("*", new [] { nameof(Description) });
    }
}

Please notice: this is a server-side validation. It doesn't work on client-side. You validation will be performed only after form submission.