I visit Cali multiple times a year in the fall and winter.

Just like Madoff did for his victims.

As I understand Federal Tax Lien will fall of after 90 days or IRS could redeem the property.

Indeed, we know that the probability that something happens to us is tiny and we won't let the media scare us.Generally I personally strive to have a balanced attitude between not falling for media sensationalism, putting things in context and looking at facts and figures while not ignoring potential problems.Hope this helps.

Honestly, most deals are going to fall into this category.

Based on your explanation, it looks like I fall into category 1 since I plan on repeating this strategy at least 2-3 more times.  

As an investor, I've seen far too many people allow their emotions get the best of them and fall into that trap.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

You would also benefit from a ranking software like Rankbreeze or Intellihost which would also show you the pricing of your comps and where you fall in the rankings of the OTA.

I work with all the big box lenders and I have worked with a private hedge fund and I have worked with smaller, local HM outfits and NONE OF THEM had anything like that.Because if the deal falls apart I am guessing they keep your 2500.