It’s that time of year when you get all of your 2008 statements in the mail telling you just how poorly your investments did last year. This week, it also fell on a day when there was no milk in the house. A major double whammy.

I was pretty convinced that we were going to come out unscathed seeing as we’re renters lucky enough to be riding debt-free. Only when we sat down to start some house buying planning did I make the unfortunate realization of just how much we lost in the stock market – money that we were banking on for a down payment. We’re basically down to where we were in 2004 which spits in the face of the painful saving we had committed ourselves to over the past four years.

America’s system makes it nearly impossible for you to live a debt-free existence, and when you try to, you wind up frankly, being screwed over by the majorities who didn’t. Case in point – do you know what a RIGAMAROLE the car dealership put us through last week when we tried to buy our car with cash? I nearly burst some internal organs with frustration. No sir, I do not want a car loan. I want to give you my money right now. Won’t you please take it?

So I think if I’ve learned anything from this it’s that the fiscal conservative always gets burned in the end. Not that I’m planning on changing my financial mindset. Quite the contrary. I’m considering becoming a full-fledged libertarian and storing all of my net worth in gold bullion underground in an Alaskan bomb shelter.

The median cost for a house in Massachusetts dropped last month to a LOW of $305,000.  For kicks and giggles, I wanted to see what I could buy with this money in the other places I have lived: Columbus, OH, Washington, DC, and South Jersey.

This is what I can get in Boston. 365 square feet in the best place in America. Extra tasty crispy.

If you’re wondering whether or not you should rent or buy, check out this sweet calculator that my dad sent to me. According to that, Matty and I are still saving money by renting (from the landlord who doesn’t cash our checks) and will be for the next 6 years. Besides, with what I’m paying to spay my dog I’d never have cash to replace the water heater.

I start off this post readily recognizing that my complaint here is unusual, and that I should actually be pretty thankful. However, when it comes to cash flow I’m a bit anal retentive and want to have all of my ducks in a row. So is any wonder that I find myself gnashing my teeth around the twenty-fourth of each month? NINE DAYS after my rent was due and PAID? And my darling landlord still hasn’t cashed the check?

It frustrates me because I’m wary to move money into the savings account until this large sum has cleared. I also start running through the many things that could have happened to that check while taking the treacherous ride through the US Postal Service. And I’m a bit of a control freak. OK, the problem is mostly in relation to that last one…

But this fear is truly grounded. When we were first married and made the move from Ohio to New Jersey, Matt ran into a bit of a snafu with a previous employer. It seemed the previous employer had overpaid him, and requested that Matt cut a check for the difference. He, being the world’s nicest person, went ahead and did just that while I snarled in the corner about how if they were going to be so stupid as to let money flow out of their pockets without looking they should have to reap the consequences, and we should keep it and do something fun! Like go on vacation! But the moral compass of the family cut the check and months and months went by.

We completely forgot about the check that was floating around somewhere in south central Ohio in the haste of oh, you know, the usual… a wedding, honeymoon, new jobs, moving across the country. And then we went to close out our bank accounts in Ohio only to be hit a week later with ENORMOUS bank fees because ex-employer decided to finally cash the check and we had closed out our bank account.

We somehow wrangled our way out of that extremely expensive situation with only a few financial scratches. But can a price be put on my increased paranoia? I think not.