Help me find a decent Comfort/Hybrid Bike that won't break the bank.

A little background: I live on a rail-to-trail, my son learned to ride last week, I am excited to go riding again. My bike is old and uncomfortable on a long ride and weighs a ton. This is my current steed: 

Yes, the mighty Quest Crestwood, purchased from WalMart in 1998 or so. Its about as bargain-basement as you can get, but it also gets the job done. The first issue I have with it is that it is heavy, a big deal because I carry it up some steps to get home from the trail and hang it from the rafters of the barn. The other issue is that I lean forward on it a bit too much and my wrists start to hurt after a while. (18" frame, 26" wheels, I am 5'10 with a 30" inseam).

So I am looking to upgrade, but a $1500 bike is not in the cards because I rarely ride and when I do, its paved roads and trails, or the packed gravel of a rail-to-trail. Even $500 is too much, that's motorcycle money. So what should I be looking for? My bike has Shimano shifters, just like the expensive ones. It has brakes just like most of the expensive ones. It has a front fork and seat post spring thing. It has 21 speeds.  It has pedals. I am not seeing anything that sets a used bike selling for $250  - $350 worth more than my $25 bike.

How do I know I can sit more upright? Larger wheels? a larger frame?  I want the seat to be lower than the handlebars. (I have already swapped the stock bars shown above with some high-rise bars). How can I save some weight? WIll "better" Shimano components really do anything, do they do more than shift gears, because mine do that.

Any names, brands or models I should be looking for? Help an old guy out so I can ride more and get some cardio. Seriously, I need cardio.

I'd look for an older Trek, Fuji, Specialized, Cannondale..

Something like this would get you disc brakes as well:

https://pittsburgh.craigslist.org/bik/d/pittsburgh-trek-ds-84/7107155446.html

I agree with dxman92 that if you go down the path of replacing your current bike, you are looking for a older used bike from one of the more reputable brands – Trek, Fuji, Specialized or Cannondale. I would add Bianchi to that list, along with specific Raleighs and GTs (both brands were purchased in the early-mid 1990s and suffered huge decreases in quality).

How can I save some weight?

You could save weight on the Crestwood, but you’ll get better bang for your buck replacing it with a new bike.

WIll "better" Shimano components really do anything, do they do more than shift gears, because mine do that.

For what you are using it for, no. Unlike cars, bike technology hasn’t progressed significantly for the type of riding you are trying to do in the last ~35 years. Yes, you can get better suspension, better brakes, carbon fiber frames, or electronic shifters, but these improvements either add expense or complexity to a bike. Any weight savings on an individual component level will be measured in grams or tens of grams.

Your front suspension fork is the equivalent of ebay coilovers – it will be heavy and perform poorly vs. a quality suspension fork. IMO, unless you are doing serious mountain biking, suspension is a marketing gimmick.

The other issue is that I lean forward on it a bit too much and my wrists start to hurt after a while. (18" frame, 26" wheels, I am 5'10 with a 30" inseam).

Moving your saddle back or tilting your saddle forward may help. The goal is to move your weight, so it is being supported by your legs, not your arms.  Another option may be to buy some handlebar extensions that allow you to move your hands from time to time or buy padded gloves.

You can get a lighter, better quality bike for around $150-250 depending on your area. I would recommend: a good condition early or mid 90’s 26” mountain/multi-trail bike and put ~2.5” street tires on it, if it doesn’t already have them.

I would avoid any sort of suspension – fork, tail or seat post. This will avoid unnecessary weight.

 I would avoid disk brakes at this price point – rim brakes will be easier to maintain and provide more than adequate stopping power.

I personally prefer steel frames, however design and tubing type will have more effect on the ride of the bike than frame material.

Just to give you an idea of what I’d be looking for, looking around my area on CL below $300 I would recommend the following (disregarding any size requirement)

https://dallas.craigslist.org/dal/bik/d/garland-vintage-bianchi-backstreet-bike/7084954187.html Overpriced

https://austin.craigslist.org/bik/d/round-rock-raleigh-technium-skylite/7109973919.html

https://houston.craigslist.org/bik/d/houston-gt-talera-tall-frame/7109841750.html

https://austin.craigslist.org/bik/d/bastrop-gt-karakoram/7092168967.html

https://austin.craigslist.org/bik/d/austin-diamond-back-outlook/7107850426.html

Any of those bikes would be lighter and have better quality components than the Crestwood. You are looking for a well maintained or overhauled bike without rust, which should be easily available in this price range.

Seems to me like your current bike with a couple tweaks for comfort is fine for your cycling goals.  

Barring something being mechanically wrong with what you have now, you're going to be seeing very small - if any - gains from a sub $500 bike.

Simply riding more often will get you the cardio.

But, if you must upgrade, I do like that Karakoram that Espartan linked.

The last Diamondback listed looks like a good bike..

SnowMongoose said:

Seems to me like your current bike with a couple tweaks for comfort is fine for your cycling goals.  

Barring something being mechanically wrong with what you have now, you're going to be seeing very small - if any - gains from a sub $500 bike.

I agree for the most part. I do think there could be some benefit in terms of weight, although I can't find a reliable source for the weight of the current bike. Maybe pinchvalve could give us the current weight? It looks like aluminum but cheap wheels/suspension fork could really add up. A lower weight would really only be beneficial for the hanging/schlepping of the bike, not the actual riding.

SnowMongoose said:

But, if you must upgrade, I do like that Karakoram that Espartan linked.

dxman92 said:

The last Diamondback listed looks like a good bike..

Both are in Austin, not Pittsburg unfortunately. I will see if I can find something local to pinch tomorrow.

Below are a few in Pittsburg - not sure about the frame sizes or if they're much lighter than OP's current bike.

These are all being sold by the same guy/gal - lots of flippers in the bike market. $250 is too high IMO,

https://pittsburgh.craigslist.org/bik/d/monroeville-street-bike-specialized/7104970765.html

https://pittsburgh.craigslist.org/bik/d/pittsburgh-specialized-mountain-bike/7104495932.html

https://pittsburgh.craigslist.org/bik/d/pittsburgh-specialized-hard-rock-blue/7103651147.html

https://pittsburgh.craigslist.org/bik/d/monroeville-90s-specialized/7103650176.html

Hardrocks were very popular in the 90's for good reason. They're also very popular now in the x-biking/gravel movement.

Another interesting potential bike.

https://pittsburgh.craigslist.org/bik/d/gibsonia-old-school-marin-bobcat-trail/7107154980.html

That Marin looks like a killer bike (maybe tires overkill for rail trails).  Then again, any of those Specialized would do the trick.

I'm a Cannondale owner.

I would stay away from Cannondale, just because they tend to think they're "innovators" like Apple does. 

Some of their parts (headsets, axles, hubs) are Cannondale specific when most other bikes use universal components.

They make stuff different just because they can. If you're ok dealing with that then don't be afraid to buy one, they are great bikes.

I'm not an engineer but the Lefty suspension fork makes me cringe.