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

Difficulty Level? 

With a Pro Membership you may be able to advance faster toward your goals

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.

I'll take the faster approach from now on. 

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

In a high demand low housing inventory environment like Oahu rents could have the potential to increase faster than less populated areas.