When I bounced this idea off of my boss, (a real estate investor himself) he said that the 2nd option is a bad choice because I would be forced to pay a capital gains tax because I wouldn't be living in the house first.

@Tom Ott is correct in saying that the Midwest is your most logical choice to invest in.

Even though my eventual goal was to work for myself as an investor, its very beneficial to work a few deals yourself just to get your feet wet.

That was a massive problem for that entire area.I think your choice not to purchase anything at the present time makes good sense and I am doing the same.

Looking for some beneficial questions that a beginner like myself might not think to ask.

Ps - there is another cash flowing quad I found as well, maybe there is someone who might be interested in some kind of mutually beneficial deal.

This is clearly beneficial to the seller as it allows potential buyers to see that the house may be still available if the present offer falls through.  

If such an order has been issued, then the seller has no choice but to abide by it until such time as a judge lifts it.

I have also been thinking about buying a condo that will be built within the next two years or so but I think buying a house, even a townhouse condo would be more beneficial in the meantime.

You will want to get this done ASAP or you could miss a month's Housing Choice Voucher Payment.