Good news, bad news
The Ranger 23 is a real good boat compared to the others in its size/price range. Is is well built, has excellent performance characteristics, and is a beautiful boat on the water. However, you will be towing a load that will be around 5000# and sitting up relatively high, due to the keel depth. That implies a hefty tow vehicle, trailer brakes, and a tongue extension that will allow it to be backed down a LONG ramp that is deep enough to float it off. Additionally, you probably don't want to raise/lower the rig every weekend - it's not a half hour job. Definitely not a setup you would want to take out for an afternoon sail. Fine for pulling out once or twice a year, but an ordeal if you did it once a month.