@Charles Roberts should chime in here as well!

I've worked with property managers for all of my other houses, but this will be a new dynamic where I self manage and live in a duplex with the tenant. 

I'll chime in here.

They will do a full underwriting of your complete financial profile.I'm sure one of the lenders will chime in here with some more specific advice, but without sufficient income nor a history of income in a commission based job it may be the path of least resistance to go with one of the national asset based lenders.

Working directly with the listing agent gets you closer to the decision maker and inherently creates an incentive for the listing agent to sell to you - they'll get BOTH sides of the commission (although they won't admit it, and they have a fiduciary responsibility to the seller, they're excited about the prospect).In addition, you'll build relationships with every conversation you have and amass a larger network of agents that can potentially bring you future pocket listings.The closer you get to the seller, the better position you'll be in.

Get a copy of the HOA bylaws and research what rights you have and what responsibilities you will inherit.

All good info in here, good luck! 

I understand what she is trying to do - act as middleman - and yes Account Closed sounds like a nice person and she can be in and out of the transaction with some money in her pocket (in the first scenario) and not look back.

It takes more time, more spreadsheets, and it's an imperfect model as rents generally rise while mortgage interest payments inherently fall (over months/years).  

She'll inherently see the success many of the interviewees have had, hear that Rich Dad, Poor Dad has been mentioned millions of times and decide to pick up the book.