14 Year in the Making... "Flip"

[Tom Peterson]

Hi.  My plan 14 years ago was to buy and hold.  But then I got interested in foreclosures.  I bought one in the Fall of 2007.  I probably don't have to tell you that my timing is not so good.  But at least time is on your side with RE, unlike my Dot Com stocks.

I realized quickly that I had to turn it into a rental.  No biggie.  Got a couple others, manage them myself.

But now I'm thinking it might be time to sell it.  It's worth more than twice what my others are worth and doesn't rent for twice.  It's profitable though.

Selling it now should pretty much pay down all RE loans. All properties are owned through an LLC. I should talk to an account, but does anyone have knowledge/advice to share?

Here are some of my concerns:

I had thought about doing a like kind exchange a few years ago but property values have gone up a lot.  I have a full time job so I doubt I could find real deals.  I'm also getting older and reducing my debt sounds appealing.

I have unrealized passive losses, I'm not sure if I could use these to offset my taxes.

Thanks, Tom