In my opinion buying a tier 1 property is a major key to this - or fixing up a property to this level.

The information and higher level of people you will be around is priceless.Frank 

Difficulty Level? 

I wouldn’t get too caught up in this question because real life experience is way more important than fancy framed certifications and degrees, but I do think that a really good IFREA will have some form of education above the high school level needed to get your real estate license.

I would like to be at the buy and hold level, however, I am not financially set to jump into that market.

That depends on you and your risk level really.

Just depends on your time and comfort level.

100 year old low-mid income rental is not really expected to have perfectly level floors.. haha Sad, but true..

I am not sure at what level it changed, but he was certain I could sell now if I wanted.  

@Charlie FitzgeraldPaying a lender off in full once you decide you no longer want to do what you said you would do is what you are supposed to do.Incidentally my first nomadic owner occupant flip, I tried to call it an investment property because that seemed like the box it intuitively best fit into (I still feel that this makes the most sense at a 'common sense' level).