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

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. 

The biggest pitfall is when a landlord tries to be "nice" - non-paying tenants are literally stealing from you, treat them like the criminals that they are.To calculate reserves for vacancy costs We average about 2-3% vacancy across our portfolio, I use 5% as the number for reserves.

Literally every time a job went south, it was on the customer.

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

Disney area is not really a cash-flow market right now unless you invest a good amount of money into theming AND you knock it out of the park with that spend.They've been building these large themed houses by the literal thousands the last few years and there are a lot of them.