But would I feel competent performing surgery on someone without an expert's guiding hand?

Not every lender/agent works with investors/househackers so if a lender or an agent can recommend someone that has knowledge in the space and can help guide you through it. 

There's a great book called Every Landlord's Legal Guide published by NOLO that will give you some great basic advice on how the process works, you may want to buy that.

I also have a close connection with an experienced developer and is willing to help mentor/guide me through looking at homes and answering my questions.

House hacking is a great way to get started.If you PM me, I'll send you my Chicago house hacking guide if you want it.

It's great to have you here.Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/m...Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/a...Read Beginner’s Guide: http://www.biggerpockets.com/r...Check out BP Money Podcast: https://www.biggerpockets.com/..

They need to be your guide through the process.  

I recently devoured the book "How to Invest in Real Estate: The Ultimate Beginner's Guide" recently...which led me to discovering this community...which is leading me to thinking about my next chapter in life.

Start with BiggerPockets Ultimate Beginners Guide (free).

This answer will guide your next move.