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.

We've seen our area MLS which covers about 20 counties come down to an average sold to list price ratio of 95.1% and Knox county specifically has come to 96.4 % which is lower by about 2% from this time last year and down from our peak this year of 98.5%. but it's about in line from winter 2022 into spring 2023 which was a time when rates were rapidly rising.

But you're dealing with an ex and that's not usually easy or fun.

I point the camera at the door so I can see if the door is closed and who is coming in.4) $5 wall mounted big thermometer I use in the winter that is in view of the camera so I can see what the temp is inside 5) Series of signs I printed (Do Use the Toilet, Make Sure to Lock the Back Door, etc etc)All mobile and I can move from property to property :)

Have fun!

@Scott ChampionPersonally, I'd pickup the vacation house for lifestyle and legacy as well as a fun project to keep busy.     

I would be using it for a medium term rental agreement during the winter months of my vacation rental.