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 need to be able to come up with this really before you spend money on a civil for plans that tells you it won't work.

Sure there is a very small chance that something will go wrong, but with the tightening rental laws spending a little on a proper lease is smart.

This would give some confidence that the property that you spend time and money vetting actually will be auctioned off. 

One of my clients that does heavy rehab and is his own GC usually spends about $10k-$20k/month during a project.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

It sent some messages with house rules  that didn’t sync correctly, pulling in info I had already updated on Airbnb.I only have one property and wanted a PMs that:-took direct bookings-synced calendars - completed simple auto messaging I like the idea of a PMS but I really don’t want to spend a lot as I’m also using Price Labs.

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

Allow a pets and I think you will have a great spot.Would adding that extra space/ spending that money be reflected in an appropriate increase in the property value too?

I wouldn't necessarily put a lot of efforts into improving/building/spending in hopes of staying booked solid, but it is a nice 'side hustle' for a pretty piece of land to bring in some extra income while it sits.