Odds of Hanging On
This is where things get tricky. Having the money will get you in, but it certainly won't keep you in.
As the hotel owner, you're responsible for literally everything that goes on in your hotel. If the sales are low, that's your problem. If the workers are on strike, that's your problem. If little Suzie flushed her toy down the toilet and now it's broken, it's...somehow still your problem.
There's also that small issue of the not-so-steady income. It's hard enough to invest so much time and money into a business, but the fact that you may or may not see a profit can be daunting and force some out of the business. This is where that previous experience really comes in handy.
It's not enough to have a lot of money; you need to have the mind (and the heart) to manage every single detail about your hotel chain. This job is not for the easily stressed, because every day will come with new challenges. Maybe all the toilets will suddenly need replacing or maybe no new guests have checked into your hotel for a couple of weeks. It's all up to you. Call it a blessing and a curse.