It's a yay for me (kinda). I am not that well-versed with the market for Bentleys, but it seems to offer a good value for money. The tech is old, but the build definitely refined.
People in the know claim a Bentley is a driver's car, while a Rolls is a chauffer's car. I like to buy my car at the bottom of depreciation because Lord knows I'll be putting miles and wearing the drivers seat if it's a car worth owning, which generally results in lower resale values; so that's my kind of car.
You've dreamed about the car and it's here. However, as you have already mentioned, it is listed a little higher than others. Then you already plan to do some repairs which will bump your true cost of ownership even higher. If you really like it as much as I think you do, then consider it and make an offer contingent on a thorough PPI (pre-purchase inspection)
This is a nice dilemma to be in, and I hope if you get it, it makes you as happy as the Fleetwood did.
I am all for making money in any way time allows, but I don't know how much demand a 13-year-old luxury car has outside of purists. Uber maybe? Prom night rentals? It might take a while before anyone comes asking to rent it out for a music video. They seem to fancy newer consumerist lifestyles.
That being said, this statement seems insensitive:
...you could rent it out to thugs for rap videos and make money on the side...
That's just me thinking out loud as I hope you don't have to get on a diet of Ramen noodles because of this purchase. Whether you did or not, it really wouldn't matter though as I have learned people value and get happines from different things. Car guys like cars, House guys like houses, Boat guys like boats etc... Being a boat guy who is pressured to buy a nicer truck+trailer to tow his nice boat and then move to a better house to match the nice truck is a sad existence. A slippery slope into the poor house.