@Eric McginnHalf the "fun" of seller financing is there are no rules... it really comes down to how well you can negotiate and how much the seller is willing to work with you. 

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

Soon enough they will see your success and want to emulate your actions.2.You will have to sacrifice a lot of your fun time.

Quote from @Jonathan Bock: Most landlords are reckless and they would do some probing for fun and to save $. 

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.

Sell the house, clear the decks, get a job, start fresh.

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.

I will definitely pay it forward as my experience grows in this fun journey! 

It is going to be roller-coaster of fun for sure.

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.