Assuming that they aren't simply lucky in market timing, excessive in leverage, or excessively risky, why do you think that some companies and leaders ARE able to duplicate the ROI driving expertise and/or improve personal-business productivity in a way that allows scalability?

I am assuming your a pretty dang good attorney, and with some experience under that belt given it's worth $500k+ to whoever, for you to do what you do.

If you would of closed at 255K Im assuming the liens would of been cleared.

Section 8 rentals are frequently located in extremely low barrier of entry markets, especially the single-family homes and small multi-family properties which I assume has also led to an influx of inventory.

I'm going to assume your PITI is somewhere in the $700-$800 range.

If they do, then you can likely find another tenant for that amount fairly easily, as I would assume the entire town's taxes are up- so if someone really wanted to be in town, that price is the new normal.If your taxes increased that substantially in a C neighborhood, your tenants would way more likely give push back for that type of increase- even though you're not being greedy, you're just imposing the same raise you were given.Often the buyer who had the "well, the numbers are better" mentality is only looking at year 1. 

That's pretty much the only way you can consistently get higher than market rent via S8.Also, don't make the mistake of assuming the S8 voucher amount is 100% for rent.

I would assume we are similar in age because you are in college.

Figure you are paying $6K in insurance for 5 years (assuming it doesn't go up) plus whatever the deductible is...is it better to save that money and should you need a new roof, pay for it yourself? 

It 12 years, assuming you make no extra payments, you'll have a paid off condo that cash flows a lot better.