It literally takes less than 10 minutes to set up free online rent payment at one of the several who offer it for nothing, and another 10 minutes to set up accounts such as Square or Stripe to collect via credit cards and other electronic payments. 

I have had messaging problems, calendar sync problems(literally the most basic thing they are supposed to do), and now it will not save notes on the calendar so I cannot recall why I blocked times as unavailable. 

I'm definitely new and I don't have all the logistics planned out this is just the vision now I'm trying to backwards engineer and figure out my steps I thought my first step would be to househack a 4-Plex on an FHA loan and then graduate to six or 12 units and then move on to bigger properties most likely outside of Chicago to your point. right now I am very confused this is the second time someone has said that four unit is not like a six or 12 but I'm not really sure in what ways is it the underwriting is it the management is it literally every aspect of it.

I had the exact same issue, literally about a year ago, but on my personal residence.

I quite literally know every single listing on the Oregon Coast and which of them is eligible for a STR permit.

Must all be level and flush.

The agent you spoke to is probably referring to the crazy boom of the covid years where buyer's literally had zero negotiating power. 

You definitely need insurance - one hurricane could wipe you out or cause enough damage to where it essentially (not literally) still wipes you out. 

----- Ummm because of what was literally just said about them in this post???

People have done this literally for thousands of years.