OK. First, I am 45, 250lbs, 5'10", moderately healthy, get a good deal of hiking and walking on a daily basis, eat well, drink moderately. That being said, I like to bike and have been wanting to get into cycling for some time. I have a "too small"; mountain bike (Giant Rincon) with semi-slicks. I like to bomb on moderate off road and gravel and I like to ride on the road; 2/3 road, 1/3 off. I like the idea of a cross with 700cm wheels. I rode a 58cm Surly LHT and liked it, a lot, but the price was too high for my first "good" bike. I have not taken a Surly Cross Check out yet. I would like to get into an entry level bike that would fit the moderate specs I am looking for and be in the less than $500 range. Older is fine. I would prefer steel. I would likely prefer used (because of price). I'd like something I can ride to get a feel for riding in general and to expedite the "getting back in shape" process. So, any suggestions? Thanks for any help you can provide.

Where do you ride?

https://athensga.craigslist.org/bik/5985304109.html

https://athensga.craigslist.org/bik/5991493863.html

https://athensga.craigslist.org/bik/5979509309.html

If buying used, itd be best to look for what in your area fits you fromba sizing perspective, then factor in use and price to decide what will be best.

I could suggest 15 different bikes which fit your desired criteria, but if none are available in your area in your size, then what i suggested is useless.

Around the country roads, parks, paved and dirt trails and gravel roads.

Just speaking for myself, I'd also look at the weight factor.
I starting riding seriously 5 years ago. I wanted to pay around $300. I found a good Trek that was 10 years old and in good shape. (I forgot the model, I sold it on ebay). The reason I sold it was that one day I decided it was too heavy.

At my age, those hills on the greenway were getting more and more laborious, so I weighed my bike and said to myself: "I'm carrying a 15# sack of potatoes up those hills" because my scales said 31 lbs. I was depressed for a few weeks. Well it sold pretty fast on craigslist.

The very next day, I saw an ad on craigslist for a Fuji that weighed 18 lbs. I bought it immediately, and the hills are a lot easier now. With all the new material they have now, it will support you fine.

Good luck.