I have horse blinders on, when it comes to looking at other markets- I am focused on my own area.

Don't buy real estate if you don't have money or easy access to it.Unfortunately, for most of us, slow and steady still wins the race.

Beating a dead horse here but Zoning & Restrictions.

One thing to consider with condos is that it can be race to the bottom, once a few nervous owners start lowering rates to get higher occupancy, more and more do it to fill up their calendar, so you end up with $100 night.

The argument there goes that the house is more valuable as a short-term rental (which to beat the horse, it's not permitted for) and I would counsel my clients to not buy at the $330k purchase price. 

Sometimes all it takes is one to get you out of the rat race.

@Derek Raivio  ok this is just me: If I had that kind of collateral in a deal like that, I would find one partner with some real horse power even if that partner will take more of the pie than a group of investors.

Let the first one season for 12 months to make sure you can actually make money.I heard of a guy that bought 2 pretty quick and then sold 2 even quicker because he was losing money at todays inflated RE prices and higher mortgages.Slow and steady wins the race.

Retiring, "getting out of the rat race", etc... are NOT financial goals. 

I'm just getting started and similarly have a 3 year goal of financial freedom away from my rat race job.