Since this post didn't get any replies, I'm going to reply with what I ended up doing incase it helps anyone else later.

Hello and thank you for this reply - yes, I have been analyzing a few properties - I have found that the main issue for both the traditional long term rental and also short term rental in this area is reliable property management - it is traditionally a cottage country tourist area, but it is becoming more popular for long term residency, and there is an emerging missing middle, because of property prices.

Thanks for the reply, I know my goals can be crazy and yes it does sound a little unrealistic but I believe it is still doable in the long run as long as I do everything right. 

Some places I am looking at include Flagstaff, Pigeon Forge, and Las Vegas.I am hoping to use this site to build connections in those areas to get "boots on the ground" information and support to find the best location.Thank you all for replying to my post.

What a thorough and actionable reply.

Sorry for the late reply, I am in the Portland area. 

@Ricky Roxbin  Did Kenny reply to you?

I appreciate your reply.1.

Hey Drew,Thanks for the reply buddy!

Thanks for the reply.