diff --git a/amanuensis/__main__.py b/amanuensis/__main__.py
index 79160ed..81a6d63 100644
--- a/amanuensis/__main__.py
+++ b/amanuensis/__main__.py
@@ -1,63 +1,29 @@
 # Standard library imports
 import argparse
+import logging
 import os
-import traceback
+import sys
 
 # Module imports
-import amanuensis.cli as cli
-from amanuensis.cli.helpers import (
-	USER_ARGS, USER_KWARGS, LEXICON_ARGS, LEXICON_KWARGS)
+from amanuensis.cli import describe_commands, get_commands
+from amanuensis.config.context import RootConfigDirectoryContext
 import amanuensis.config as config
 from amanuensis.errors import AmanuensisError
+from amanuensis.log import init_logging
+from amanuensis.models import ModelFactory
 
 
-def repl(args):
-	"""Runs a REPL with the given lexicon"""
-	# Get all the cli commands' descriptions and add help and exit.
-	commands = {
-		name[8:].replace("_", "-"): func.__doc__ for name, func in vars(cli).items()
-		if name.startswith("command_")}
-	commands['help'] = "Print this message"
-	commands['exit'] = "Exit"
-	print("Amanuensis running on Lexicon {}".format(args.tl_lexicon))
-	while True:
-		# Read input in a loop.
-		try:
-			data = input("{}> ".format(args.tl_lexicon))
-		except EOFError:
-			print()
-			break
-		tokens = data.strip().split()
-		if not data.strip():
-			pass
-		elif tokens[0] not in commands:
-			print("'{}' is not a valid command.".format(tokens[0]))
-		elif data.strip() == "help":
-			print("Available commands:")
-			for name, func in commands.items():
-				print("  {}: {}".format(name, func))
-		elif data.strip() == "exit":
-			print()
-			break
-		elif data.strip():
-			# Execute the command by appending it to the argv the
-			# REPL was invoked with.
-			try:
-				argv = sys.argv[1:] + data.split()
-				main(argv)
-			except Exception as e:
-				traceback.print_exc()
-
 def process_doc(docstring):
 	return '\n'.join([
 		line.strip()
 		for line in (docstring or "").strip().splitlines()
 	])
 
+
 def get_parser(valid_commands):
 	# Set up the top-level parser.
 	parser = argparse.ArgumentParser(
-		description=cli.describe_commands(),
+		description=describe_commands(),
 		formatter_class=argparse.RawDescriptionHelpFormatter)
 	# The config directory.
 	parser.add_argument("--config-dir",
@@ -73,21 +39,7 @@ def get_parser(valid_commands):
 		dest="log_file",
 		default=os.environ.get(config.ENV_LOG_FILE),
 		help="Enable verbose file logging")
-	parser.add_argument("--log-file-size",
-		dest="log_file_size",
-		default=os.environ.get(config.ENV_LOG_FILE_SIZE),
-		help="Maximum rolling log file size")
-	parser.add_argument("--log-file-num",
-		dest="log_file_num",
-		default=os.environ.get(config.ENV_LOG_FILE_NUM),
-		help="Maximum rolling file count")
-	# Lexicon settings.
-	parser.add_argument(*LEXICON_ARGS, **LEXICON_KWARGS)
-	parser.add_argument(*USER_ARGS, **USER_KWARGS)
-	parser.set_defaults(
-		func=lambda args: repl(args)
-		if args.tl_lexicon
-		else parser.print_help())
+	parser.set_defaults(func=lambda args: parser.print_help())
 	subp = parser.add_subparsers(
 		metavar="COMMAND",
 		dest="command",
@@ -109,23 +61,29 @@ def get_parser(valid_commands):
 
 	return parser
 
+
 def main(argv):
 	# Enumerate valid commands from the CLI module.
-	commands = cli.get_commands()
+	commands = get_commands()
 
+	# Parse args
 	args = get_parser(commands).parse_args(argv)
 
-	# If the command is the init command, a config directory will be
-	# initialized at args.config_dir. Otherwise, initialize configs using
-	# that directory.
+	# First things first, initialize logging
+	init_logging(args.verbose, args.log_file)
+	logger = logging.getLogger('amanuensis')
+
+	# The init command initializes a config directory at --config-dir.
+	# All other commands assume that the config dir already exists.
 	if args.command and args.command != "init":
-		config.init_config(args)
+		args.root = RootConfigDirectoryContext(args.config_dir)
+		args.model_factory = ModelFactory(args.root)
 
 	# If verbose logging, dump args namespace
 	if args.verbose:
-		config.logger.debug("amanuensis")
+		logger.debug('amanuensis')
 		for key, val in vars(args).items():
-			config.logger.debug("  {}: {}".format(key, val))
+			logger.debug(f'  {key}: {val}')
 
 	# Execute command.
 	try:
@@ -134,6 +92,6 @@ def main(argv):
 		config.logger.error('Unexpected internal {}: {}'.format(
 			type(e).__name__, str(e)))
 
+
 if __name__ == "__main__":
-	import sys
 	sys.exit(main(sys.argv[1:]))
diff --git a/amanuensis/cli/helpers.py b/amanuensis/cli/helpers.py
index 5bcf4fe..1d2a136 100644
--- a/amanuensis/cli/helpers.py
+++ b/amanuensis/cli/helpers.py
@@ -2,12 +2,19 @@
 from argparse import ArgumentParser
 from functools import wraps
 from json.decoder import JSONDecodeError
+from logging import getLogger
+from sys import exc_info
+
+logger = getLogger(__name__)
 
 
-# These function wrappers allow us to use the same function for executing a
-# command and for configuring it. This keeps command arg configuration close to
-# where the command is defined and allows the main parser to use the same
-# function to both set up and execute commands.
+#
+# The add_argument and no_argument function wrappers allow the same
+# function to both configure a command and execute it. This keeps
+# command argument configuration close to where the command is defined
+# and reduces the number of things the main parser has to handle.
+#
+
 
 def add_argument(*args, **kwargs):
 	"""Passes the given args and kwargs to subparser.add_argument"""
@@ -47,13 +54,21 @@ def no_argument(command):
 	return augmented_command
 
 
-# Wrappers for commands requiring lexicon or username options
+#
+# Many commands require specifying a lexicon or user to operate on, so
+# the requires_lexicon and requires_user wrappers replace @add_argument
+# as well as automatically create the model for the object from the
+# provided identifier.
+#
+
 
 LEXICON_ARGS = ['--lexicon']
 LEXICON_KWARGS = {
 	'metavar': 'LEXICON',
 	'dest': 'lexicon',
 	'help': 'Specify a user to operate on'}
+
+
 def requires_lexicon(command):
 	@wraps(command)
 	def augmented_command(cmd_args):
@@ -67,34 +82,33 @@ def requires_lexicon(command):
 			return None
 
 		# Verify lexicon argument in execute pass
-		val = (getattr(cmd_args, 'lexicon')
-			if hasattr(cmd_args, 'lexicon')
-			else None)
+		val = getattr(cmd_args, 'lexicon', None)
 		if not val:
-			from amanuensis.config import logger
-			logger.error("This command requires specifying a lexicon")
+			logger.error("Missing --lexicon argument")
 			return -1
-		from amanuensis.lexicon import LexiconModel
-		cmd_args.lexicon = LexiconModel.by(name=val) #TODO catch specific exceptions
-		if cmd_args.lexicon is None:
-			from amanuensis.config import logger
-			logger.error('Could not find lexicon "{}"'.format(val))
+		try:
+			model_factory = cmd_args.model_factory
+			cmd_args.lexicon = model_factory.lexicon(val)
+		except Exception:
+			ex_type, value, tb = exc_info()
+			logger.error(
+				f'Loading lexicon "{val}" failed with '
+				f'{ex_type.__name__}: {value}')
 			return -1
 		return command(cmd_args)
 
 	augmented_command.__dict__['wrapper'] = True
 	return augmented_command
 
+
 USER_ARGS = ['--user']
 USER_KWARGS = {
 	'metavar': 'USER',
 	'dest': 'user',
 	'help': 'Specify a user to operate on'}
+
+
 def requires_user(command):
-	"""
-	Performs all necessary setup and verification for passing a user to a CLI
-	command.
-	"""
 	@wraps(command)
 	def augmented_command(cmd_args):
 		# Add user argument in parser pass
@@ -107,18 +121,18 @@ def requires_user(command):
 			return None
 
 		# Verify user argument in execute pass
-		val = (getattr(cmd_args, "user")
-			if hasattr(cmd_args, "user")
-			else None)
+		val = getattr(cmd_args, "user", None)
 		if not val:
-			from amanuensis.config import logger
-			logger.error("This command requires specifying a user")
+			logger.error("Missing --user argument")
 			return -1
-		from amanuensis.user import UserModel
-		cmd_args.user = UserModel.by(name=val) #TODO catch specific exceptions
-		if cmd_args.user is None:
-			from amanuensis.config import logger
-			logger.error('Could not find user "{}"'.format(val))
+		try:
+			model_factory = cmd_args.model_factory
+			cmd_args.user = model_factory.user(val)
+		except Exception:
+			ex_type, value, tb = exc_info()
+			logger.error(
+				f'Loading user "{val}" failed with '
+				f'{ex_type.__name__}: {value}')
 			return -1
 		return command(cmd_args)
 
@@ -140,15 +154,16 @@ def alias(cmd_alias):
 # Helpers for common command tasks
 
 CONFIG_GET_ROOT_VALUE = object()
+
+
 def config_get(cfg, pathspec):
 	"""
 	Performs config --get for a given config
 
-	cfg is from a with json_ro context
+	cfg is from a `with json_ro` context
 	path is the full pathspec, unsplit
 	"""
 	import json
-	from amanuensis.config import logger
 
 	if pathspec is CONFIG_GET_ROOT_VALUE:
 		path = []
@@ -162,6 +177,7 @@ def config_get(cfg, pathspec):
 	print(json.dumps(cfg, indent=2))
 	return 0
 
+
 def config_set(obj_id, cfg, set_tuple):
 	"""
 	Performs config --set for a given config
@@ -170,7 +186,6 @@ def config_set(obj_id, cfg, set_tuple):
 	set_tuple is a tuple of the pathspec and the value
 	"""
 	import json
-	from amanuensis.config import logger
 	pathspec, value = set_tuple
 	if not pathspec:
 		logger.error("Path must be non-empty")
@@ -178,7 +193,7 @@ def config_set(obj_id, cfg, set_tuple):
 	try:
 		value = json.loads(value)
 	except JSONDecodeError:
-		pass # Leave value as string
+		pass  # Leave value as string
 	for spec in path[:-1]:
 		if spec not in cfg:
 			logger.error("Path not found")