Given my (novice) experience level, I am looking for relatively newer units to avoid running into any maintenance costs that older units may offer.

I don't know what your experience level is but you will need an aggressive and knowledgeable Realtor.   

I’d love to change it to a 5-star if I could.”Then I start the process of trying to get it changed...which is somewhere above brain surgery but below putting someone on Mars in terms of difficulty level. I

However, I view the offer we made as aggressive for the current risk level.  I

What is your experience level? I

I have a great head on my shoulders and more then enough drive to get to whatever level I need.

I want that initial investment back ASAP ao i can play with "house money". 

., is it better to start house-hacking in an expensive market (how can I even get in), or go out-of-state where entry-level is more approachable.

Investments and primary residences are not treated the same.Several people have shared the rules regarding a primary residence for federal tax purposes.If this was your home for 2 of the past 5 years, you are allowed $250k cap gain exemption as you are single.Your income level is irrelevant. 

Not sure what your experience level is in real estate whatsoever... so if you are a mobile home investor, I'll respect that... but I don't think buying into a mobile home park is a good investment VERSUS traditional real estate.