If you’re still weighing your options between Salem and Portland, I’d recommend Salem for its easier entry points and cash flow potential, particularly for a BRRRR newbie.

BP also has a great rental property tool that will help you to analyse potential properties. 

I’m not sure how common these situations are but I figured if I’m having to go through it and learn the process of this situation maybe I can share it and potentially help others 

They are getting what they really want, and you are crafting the deal to where it will still make sense for you.One potential issue is if what is most important to them is also important to you.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

Look for neighborhoods with strong rental demand and potential for appreciation.

You have to weigh the cost of a non-renew against the potential income you could make. 

Less buyers are attracted to these properties for a reason and they are priced accordingly.

If anyone has any advice on how I should try to get a solid mortgage or how to leverage my first time home buyer benefits, please reach out.

It seems like you aren't working with the best team... they could have given you better advice.That said, I would consider potentially sticking it out unless the burden of the HELOC is too much.