i.e. how'd you overcome that initial fear. 

Some of the questions that tun through my mind is, if I leave my job and move to Florida, what will I do for income in the meantime while i work on purchasing a property.I’m currently living in Boston and want to move back to Florida soon so I can house hack.Any advise on how to just take the step and overcoming my fear?

It can't simply be overcome by people saying to you, "Go on, get out there. 

It's fast-paced and written in plain language that explains the complexity of overcoming strong opposition to change.

Hopefully I can overcome this, and learn from seasoned investors in my area.

Your concept is not completely blurred, however, the first hurdle you must overcome are the legalities of unlicensed wholesaling in your state.

My greatest challenge is that I'm just not good with all the technology, including REI Blackbook, but I'm working on overcoming that.

But I'm not too concerned yet, because they have a lot of challenges to overcome:1.

But of course, your administration may easily be able to overcome that potential weakness.

On the flipside, I'm sure the experts are tired of hearing of beginners looking for help but not following through or staying committed.My thought to overcome this dilemma is to start analyzing deals (using bigger pockets software or an excel template) and ask an experienced (hopefully local) investor to check the inputs and assumptions and explain how/why they would tweak the model.