I'll preface this by saying that I haven't test ridden any of the bikes I'm thinking about - it's all been virtual comparisons and brainstorming. Obviously any purchase would require a thorough test ride of many of the bikes I'm thinking about and the appropriate geometry comparison for any special order bike.

Although I won't be buying for several months and maybe up to a year, I've already begun the research and would like to elicit a few opinions.
Currently, I have an XL 2006 Specialized Sirrus as my primary bike and sole commuter. My wife has a 2005 Trek 7300 in a 20" frame that I can ride comfortably, but I would only use a temporary back-up. I've got the Sirrus outfitted with rack, fenders, panniers, lights - the standard commuter package. I currently run 25 mm armadillo tires and have not had a problem, but if I get a second bike for the below listed reasons, I'd consider running a little wider tire as this bike will pretty much be completely dedicated to commuting. I commute 3-5 days per week and do 1-2 fitness based rides per week on top of that (usually 15-25 miles) right now.

Anyway, I'm looking for a second bike primarily for afternoon training rides with a couple of cyclist friends of mine (both are cat 3 racers) and longer weekend rides. I'm not looking to race anytime, but would consider doing event rides or centuries in the future. I live in the greater Houston Bay Area and it's extremely flat with just a few offroad options in the area, therefore the vast majority of my training will be on the roads, which are ok. There is still a lot of road debris, potholes and rough stretches on the roads around here though.

My initial thoughts were to buy a racing bike such as the Specialized Roubaix, Jamis Quest or Trek Pilot. Something designed with comfort and speed in mind. While this makes a lot of sense for keeping up with my cyclist friends, works fine for training rides on the weekend and would likely be fine for a century, it leaves me with the least versatility in my second bike.

So, I considered a touring bike such as the Trek 520, Surly LHT, Bruce Gordon BLT. These bikes could convert into my commuter at some point, would allow me to do some touring at some point (this is at least 10 years away - I've got a 2 year old and another due in a week or two), and would work well for event rides or centuries and would even allow for some rougher riding conditions compared to the racing bikes. But the reality is that I won't be doing any touring for a long time and already have a solid commuter that I really like, so this seems like not the best fit. Still, it's worth considering.

Finally, comes the cyclocross bikes such as the Surly Cross-Check, Jamis Nova, Kona Jake the Snake, Trek XO-1. I really like the idea that this bike could be used a commuter some time down the road, could be used off-road (I'd like to do some off-road riding, but this would only be for a fun change of pace and is not a priority) and overall would still be fairly speedy on the road although the gearing isn't optimal for pure road cycling.

Honestly, I don't know which way to lean and I luckily have all the time in the world to decide, because I don't have the cash right now - I will in the future. I'm looking primarily in the $1000-$1500 land and would like to at least have 105 components. Given a very convincing story I'd consider going up to $2000, but I'd prefer to use those extra hundreds for appropriate accessories.

Thought I'd at least show a pic of my Sirrus also. I've since replaced the rear trunk with Arkel T-28 panniers, but otherwise, everything else is current about the bike.

LOL! I'm seriously contemplating gettting a THIRD bike!

I have a Bruce Gordon BLT and while I keep up with the B class or more active club riders here I wouldn't use such a heavy frame for riding with Cat 3 types. Bruce does make regular bikes, custom even, but not in your price range. Get one of the credit card touring bikes. Rei has two. There are lots. The Sirus looks fine for commuting until you go 20 or 30 miles or more each day. PM the names on my commute distance poll that go the distance you need to go and see what they ride. You do not have to wait years to go touring. Little kids in a trailer. Older kids can ride a tandem or their own bikes.

if i wanted to keep up with roadies but still keep some versitility i'd be buyin this bike.


https://www.jamisbikes.com/bikes/06_nova.html

the new colors look cool to! and evryone knows how important that is

Take a look at the Specialized Tricross. A cross bike, it is a pretty sweet street ride, especially if you put some thinner tires on it.

If your CAT 3 riders are anything like the ones here [yours are likely faster], I'd stick with something a little less touring-oriented. The Jake the Snake and Trek XO-1 are both excellent bikes, and I imagine the Jamis is great, although I'm not as familiar with that model. I've been on the Roubaix, and it's comfy. Veeeeeery comfy. The wheels, frame, fork and position all contribute to smooth out everything you might encounter. At the same time, it's still pretty light, and has a reasonable parts pick. If you're 10 [or 5] years away from touring, you might as well buy a bike you're going to use and enjoy now.

Excellent points to consider. Touring is probably the farthest option away and would be the ideal bike to replace my Sirrus as a commuter, so I'll save the touring frame for later.

After talking with one of my cat 3 rider buddies, I got the idea of potentially doing a 3 bike lineup - Sirrus as the commuter, pure road bike and pure mountain bike. This way you have 3 bikes suited for their exact purpose.

I think a higher end cross bike would do the job just fine on the road, but to take it offroad, I'm not sure if I'd need a different cassette and wheel set to go with beefier tires.

Thus, here's the simplified math I'm using. Since I'd need to get shoes and pedals for either option and 1 set would do, those cancel each other out.

Ideal Riding Scenario
Commuter - 3-5x/week
Road Bike - 1-2x/week
Mountain Bike - 1-3x/month

Option 1 - Road and Mountain Bike

105 Road Bike - $900 to $1300 (Trek 1500 to Specialized Roubaix/Trek Pilot 2.1)
Basic Hardtail MB - - $350 to $550 (Specialized Hardrock to GF Marlin)

Total - $1250 to $1850

Option 2 - Cyclcross bike with 2 wheel sets

Bike - $900 to $1500 (Bianchi Volpe to Redline Conquest Disc)
Changing cross tires to road tires - $30 to $50
Second wheel set, tires, cassette - $200 to $400

Total - $1130 to $1950

So overall, it seems that for the same money, you could get 2 bikes ideally suited for their intended purpose rather than use a cross bike to try to hit both ends of the cycling spectrum.

Looks, like I'm test driving the road bikes first. I'll look at mountain bikes second and years down the road, I may switch my Sirrus to a cross or touring bike.

You talked to your cyclist friends and are now considering three bikes. Classic.

Actually... I agree. For 1-3 times a month mountain biking you probably don't need anything too fancy. I would go for a fast road machine, keep the Sirrus for commuting and look at used mountain bikes. I would go with something rigid, or at least hardtail. Suspension technology seems to change about every week.