I picked up about 20 units the other winter back, and burned through $200,000 in repairs quicker than you could write a check, and I have my own rehab crews that work full-time at this game.

    With the 5% down being sent to the escrow company (not to the seller), and standard inspection and appraisal contingencies, this seems like a very standard contract albeit with some quicker then average timeframes. 

I guess my thinking is:Previous Job = Immediate Pay Increase = Quicker acquisation of a House Hack Property = Closer to my RE and personal goals.Once I were to acquire the house then I will pursue PM as a career no doubt about it. 

That would allow for quicker turn around so you don't waste rentable days.

There are some other tricks that will allow you to take back ownership quicker if you have to so seek out someone with superior RE skills and legal knowledge in your area. 

[I don't really want to hear the "I'll be able to get out of debt quicker" argument, because, what's stopping you from already doing that?]

Fees for violating the CC&Rs or any resolution must be "reasonable," and $2k for merely failing to provide a copy of your privately held contract with the renters is NOT "reasonable."

I am having a hard time estimating which approach is best and/or which approach would get to me my goal of having an owner occupied property quicker?

Because I am a bit older (late 50's) I was hoping to cash flow with a 15 to 20 year note so as to quicker build equity while still being profitable. 

So there are multiple benefits to contacting the listing agent directly, 1 I don't flood my agent with petty questions, 2 It is much quicker to ask the questions that are missing from the listing. 3 I can tailor specific questions per property. 4 There is no back and forth which limits misunderstandings.