Fun fact, >98% of every property on the MLS, was an off-market property until the agent/broker put it on the market.     

My dad once said if it isn't dangerous it wouldn't be fun. 

Than did all the red-tape fun to get things set, and completed soil corrections. 

You think the ones that are taking action against you are doing it for the fun of it? 

Yes, getting sued is a risk factor and I've been involved with frivolous lawsuits which are not fun, but in my opinion you'd be in a much better spot owning a property in your personal name that let's you keep an extra 10-20% of the purchase price in your pocket as emergency funds, as opposed to buying the loan under an LLC that requires every last penny you might have to make the higher down payment, then you have to operate on a shoestring.

Heck go to the casino and put it on roulette wheel of black or red. 

I love the casino so I am not one to talk.  

That was a lot of fun, but if you’re looking for a place that suits you right away or planning to buy a home, having a bit of guidance can go a long way.

Without a financial education - it's hard for him to discern which.What he should NOT do is to buy toys or spend it on fun because it'll quickly be gone.If he was financially savvy or versed in real estate - he could even buy a small apartment complex and self manage it if he had some property management skills.Advice should be catered to him specifically though, blanket advice isn't that helpful.

You can track income and expenses consistently using software or spreadsheets.As you scale, if bookkeeping isn't fun, consider hiring a bookkeeper for a couple hundred bucks per month.