New Bike for 2020 Triathlon

Ya, you aren't going to find anything new in that price range.  Watch the used bike listings though.  Something that was fast 10 years ago is still going to be fast even if the manufacturer has come out with something newer that the previous owner feel the need to burn a few thousand dollars on.  For my first race, I had a bike budget of $300.  I thought I would find a decent street bike for that price.  As I looked at the price of clip-on aero bars I realized that unless I got the bike for free they would be out of the budget.  I lucked out and found a 15-year-old aluminum frame Triathlon bike with an aero frame design.  It was a very good find and they came down from the $320 asking price to $300.  It had good component groupsets, an upgraded saddle (that would cost $300 on its own), it was well maintained, it was in good condition, and it didn't hurt that it looked really flashy and got compliments from everyone that saw it.  It was also really fun to ride.  It had some drawbacks in that it was not really adjustable and could not move to the best position for me to ride in.  It also has 650C wheels which made tire shopping difficult.   It was a 9-speed.  I replaced it with a 10-speed 700C carbon frame bike that was half its age and met the spec given to be by my bike fitter.  I kept my first bike as my "B" bike and am as fast on it as my "A" bike that I spent $1500 on used.  Whatever you get, make sure it is fun to ride.  If it fits well the bike will be fun to ride if it doesn't fit fell then you won't like it and won't stick with it.

Welcome Justin,

A new "entry level" road bike from your local shop is likely to run you $700-800 before you add anything else like pedals.  Nothing wrong with "entry level" though.  Many of the bike frames come from the same factories in China and at that end are almost all the same Shimano components.  

You *can* go somewhere like bikesdirect.com and get bikes under $500.  However...you'll likely make up much of the difference paying the local shop to assemble and/or tune up the bike and run a basic fit setup.  (These are usually included in the price of bikes they have on the floor.)  

Alternatively, you can go the used route.  Your local shop might have a selection of used bikes in addition to the new ones.  You *can* do CL or garage sales.  (I've bought used bikes off E-bay well before CL was viable.)  I put about 1500 miles on an old Raleigh and I've put over 5000 miles on an old Klein bought through E-Bay.  A caution about this route...there's no such thing as a "cheap bike," especially one you're buying sight unseen.  Expect to put new tires and tubes, new brake pads, possibly a new chain, and probably a tune-up on that bike.  This gets pricey if you're paying the local shop mechanic for all of this.  For a locally purchased bike, consider paying the mechanic at the shop for a pre-purchase inspection (if you're especially lucky, he'll already be familiar with it because the current owner had it maintained at the shop).  

Edited (I thought you had a second post mentioning bumpy ride).  If your biggest objection with the bike you have is a bumpy ride, you can probably get different tires for $30-40 apiece rather than a whole different bike.  Do some homework, but you might be able to swap 700Cx35 tires for 700Cx32 or 700Cx28 with 700Cx25 without changing rims.  700C would be the rim diameter and the x## the approximate width of the tire in mm.  Narrower tires usually require higher pressure and are considerably lighter weight.  Just looking briefly, within a single tire, going from 700Cx35 to 700Cx32 is about 2 ounces lighter (and this is rotating mass) and probably runs 5-10 psi higher pressure.