As the types are not compatible (and you will generally want to avoid code-behind/dependency properties) a "string to enabled converter" is your best bet for this type of simple check.
As converters are shared around projects, and are only a minor entry in the XAML (and no changes to code-behind) you should not be worried about using converters... converters are your friends :)
Start making a library of useful converters as the same sorts of problems occur time and time again.
Here is some minimal code (no error checks) for a converter that does what you wanted:
using System;
using System.Windows.Data;
namespace LengthToEnabledTest
{
public class LengthToEnabledConverter : IValueConverter
{
#region IValueConverter Members
public object Convert(object value, Type targetType, object parameter, System.Globalization.CultureInfo culture)
{
if (value is string)
{
return (value as string).Length > 0;
}
throw new NotImplementedException();
}
public object ConvertBack(object value, Type targetType, object parameter, System.Globalization.CultureInfo culture)
{
throw new NotImplementedException();
}
#endregion
}
}
and some matching test XAML (a simple stack panel with 1 textbox and 1 pushbutton):
<UserControl x:Class="TransitioningContentContolTest.LengthEnabledTest"
xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
xmlns:converter="clr-namespace:LengthToEnabledTest"
mc:Ignorable="d"
d:DesignHeight="300" d:DesignWidth="400">
<UserControl.Resources>
<converter:LengthToEnabledConverter x:Key="LengthToEnabledConverter"/>
</UserControl.Resources>
<StackPanel x:Name="LayoutRoot" Background="White">
<TextBox x:Name="textBox" />
<Button Content="Press me" Height="20" IsEnabled="{Binding Text, ElementName=textBox, Converter={StaticResource LengthToEnabledConverter}}"/>
</StackPanel>
</UserControl>