Granted we only have 17 but still, I’ve never used anything except a simple excel spreadsheet and all my rental properties have a separate savings account under my main account at my local bank.

However, I also think that a lot of people who set out to pursue this strategy miss the fact that it is literally a lifetime commitment to deferring taxes, which by definition means not realizing the gains.

Anecdotally, if a house that literally 'floats' over water can burn by wildfire, is any property truly insurable? 

It's not simple, it's not easy and it sure as hell isn't a sure thing. 

Most of the time it's "mehhhh"....I can literally selling this service to buyer lol

That's a LOT of $ to go to AZ, TX, FL, literally anywhere. 

If I didn’t have a positive experience with them prior to this, I would literally think we were scammed.

Something simple along the lines of, no pets due to small shells and turf located at property that may hurt pets, would dissuade even service animal owners.  

I'm not satisfied with not filing the rental in an LLC simply because it's more simple and might cost me an additional filing fee .

Dan,The process to create an LLC in Illinois is pretty simple.