This is a really personal question specific just to you.  

If you do rent to this person, don't act shocked when they fall behind or don't pay at all.

Personally, I would just deny them.

There's some connection you have to this person with money who is looking to invest it short term and collect an x% return. 

Have both a personal and REI emergency fund because life happens.   

I personally wouldn't invest in a property that doesn't cash flow.What is your financing strategy? 

You will be sued personally and everything in your personal name is unprotected.

Easy to make updates and reprint to put in nice 3 ring binder.Many people are not logged into Vrbo besides person making reservation and appreciate being able to easy get information.

My educational background is in science, but my personal background is rooted in the Midwest where I grew up on a farm and gained a skillset in everything mechanical. 

Quote from @Kenzer Hodgson: Quote from @Trent Reeve: personally, i think a dynamic pricing tool will pay for itself (should be around $20/month). it will help with far out/near time pricing, minimum stays, etc.