I'm also a big fan of audiobooks since they are pretty convenient to listen to when you have free time.

Should the properties be valued closer to market value or am I essentially paying a “convenience” premium because the portfolio has already been built?

The MF is the best option for you but then there is still a need for spending time property managing which is not always convenient. 

I personally stick to one area (currently), and the overriding factor is proximity to my personal residence, to my full-time project manager and to my contractors.While I certainly wouldn't be investing in this area if it weren't profitable, I'm happy to forgo some potential profits for the convenience of dealing with investments in close proximity to where I live.

But I am in NY so 500-1000 dollars is really not going to earnestly buy me anything, except maybe being laughed at by a banker5000 could maybe be a consideration on a low to mid property but I don't want to gamble that my first deal will be perfect...

I don't have enough money to speculate (gamble) with real estate.

However, I hate the thought of putting my neck on the line for what is essentially gambling, without getting that nice monthly inflow that makes it all worth it.So, I am thinking of investing in a town about 2 hours away.

They looked for opportunity and then fought like the devil to make something out of that opportunity.BTW, by new techniques I'm not referring to the internet (went to high speed 2 days ago from dial-up), blackberries (don't have one), or any other modern convenience like cars and phones.

Time for a quick chat with your lawyer.Given you're now in this situation, I would call her and tell her you will provide one time at your convenience when she can come and take everything she's left behind.

You could buy a house that actually cash flows a few hundred dollars per month and that is in a location that is more convenient to where you are located now.