My career has been in IT where I've honed skills in people and project management.

For now, I am looking to use my negotiating/sales/marketing skills to capitalize on the wholesaling market.  

It looks like you have a good background with skills that will transfer well to RE investing.

In full disclosure my business partner is the President of the REIA and I am an active component in it as well, but it is a great place to network and learn new strategies and skill. 

This starts with educating yourself on values, furthering your knowledge base on the technical side, sharpening your negotiation skills, and working on your belief system.

@Jd Martin @Brent Coombs  I always knew when the Guru's had come through PDX.my agents would come running to me about this big time investor that was going to buy 5 props a month.I would tell them to invite them to lunch ( my treat)  I did this to size them up.. 99%  No Money no skills and just looking to abuse my poor agents.. did I feel bad when I flushed them out and put them in their place at lunch ...

I don't believe that much expensive software is a necessary expense, plus you'll have to find special skills that can operate the software.

I believe that working as a real estate agent will give me plenty of great experience and knowledge to improve my confidence and skills as an investor.

It's "sketch", as the kids say.A better solution would be to build a lead generation system with your WP skills.

At that point, a 100-unit property isn't much different in skills and experience needed.Regarding private investors, every investor needs to evaluate risk, not just return.