September 2015 - Route to Retire

I Got a Second Opinion Last Week…

So, I had been talking with one of my mentors a couple of months ago and we got on the subject of taxes… particularly taxes regarding rental property. If you’re a regular follower of my site, you know that I currently have one rental house and I’m looking for a second so this was an important topic for me. My friend that I was talking with has five rental houses and is extremely savvy when it comes to the financial details of this arena, so I definitely listened intently. In short, what I decided after this discussion was that I needed a second opinion on my taxes. For the past 15 years, I’ve done my taxes through TurboTax. It started out pretty easy… just

Should I Pay Off My House Early?

You’ve been doing well with your finances. You don’t have any car loans or credit card debt. You’ve been socking away money in your 401(k), Roth IRA, and other investments. Now you’re looking for more avenues to help put yourself in a better position with your money. Eventually, you start asking yourself that one question… the one that can really stir up some good debate… Should I pay off my house early if I can? On one hand, you have that huge feel-good aspect of getting rid of that giant burden that you’ve had for years. A mortgage payment is a real thorn in anyone’s side – no one likes paying that bill every month. I had a major debt problem coming out of college

Four Weddings and Maybe My Funeral…

Today I’m getting slightly off track because I need to rant and, well, it’s my blog so I’m going to go for it! Ok, first off, maybe four weddings is an exaggeration… I have three to go to in the next month. And maybe it’s not really going to be my funeral, but it sure feels like it! Here’s the problem… Wedding number one is out-of-town – it’s in the big city… New York City. I hate the big city. I’m a suburbs kind of guy. I don’t care for the hustle-bustle of big cities like Chicago and, even though I haven’t been there before, I’m going to assume NYC as well. Now, I know a lot of you live for

Should You Compromise Your Lifestyle to Retire Even Earlier?

If you’re reading this right now, you’re most likely either looking for a way to retire early or you already have a plan in place. Either way, the thought repeatedly comes to my mind of ways to make retiring early happen even sooner. I run an interesting gamut of being frugal with most things but still splurging by taking cruises and other fun vacations on a regular basis. It drives me nuts to waste money on things I have the ability to control and I spend a fair amount of time trying to decrease these costs. A good example of this is cable TV. We’re now at the point where a lot of people are starting to find ways to “cut