The AG does have some egg on her face with a recent article talking about potential conflict of interest in her pursuit of Lender Processing Services.

Deductions are permitted for expenses incurred in the pursuit of profits ...

So, would the career path of a commercial or residential broker be best suited to help me in my pursuit of acquiring a sizable rental portfolio over the next 6 years?

While I normally wouldn't consider using debt to cover an expense like a home remodel, true dedication to earning a CoC return in a pursuit that so seamlessly synergizes with your short and long-term goals might make this an exception to where that could be a potential benefit.

If the community checks out, my girlfriend and I will be relocating to Norfolk in pursuit of investing, supplemented by our full time jobs. 

You could fund the pursuit costs for 6 sizeable (100 unit) multifamily properties with 300k and end up with all of your money back and hundreds of units in three years.

I decided to start my new career in long term holding rental properties instead of flipping, in pursuit of the financial freedom aspect of it.

I am currently in pursuit of a home for myself in a very hot niche market, and the strategies you have mentioned (with the exception of a JV) usually fail as offers the great majority of the time because the sellers get the cash they want and walk away - no strings attached.  

I find it simplest to start the life span count down when installed and estimate its monthly replacements cost across all months of the life of the item.Again I am not trying to be discouraging as I think it is great you have started your REI pursuits. 

I use this link to find stories and quotes to maintain my sanity in my pursuit of REI Success.