Air Travel Roulette (updated)

So I'm trying to book my flight to Reno for the spring bridge nationals. My first choice was to use my credit card miles. So I call them up, and after staying on hold for about half an hour, the journey begins. First, they notify me that ticket redemptions require a 21-day advanced travel booking. So I can't redeem a full ticket, but I can use the points for dollars option. Except that it has to be on the lowest priced fare, which was an early flight out of JFK with two stops in San Fran and LAX travelling on turboprop planes once I was on the west coast.

Full price it is then. Time to do my own search, courtesy of kayak, priceline, the airlines' own websites, etc. Didn't there used to be a good reason to book round trip flights? Besides the convenience of accumulating miles with the same airline, didn't it cost less because they were guaranteeing your purchase of two flights ahead of time? As I look at all the offers around, I don't see round trip bookings any cheaper than two single flight bookings.

Since I no longer have any loyalty to any airline (fck you United for letting my college miles expire with no warning), I am in the process of choosing two separate flights. Seems to me to be the best deal in this age where round trip doesn't seem to be rewarded. It looks like I'll have to get to LaGuardia for a 7am flight into Reno, and it'll cost me a good amount extra on the way back to avoid a redeye. This sucks.

You know how your credit score goes down the more times you pull up your credit report? I wonder if these sites work on a similar model. If you make search requests for the same flight over and over, I wonder if they start charging more because of a "perceived" interest in the route?

UPDATED: Ok, booked my flights. Into Reno on American, one stop in Dallas, both routes jets. $140 including fees. The bad thing is it's a 7am flight out of LaGuardia. Back out on United, one stop in Denver, both jets. $240 including fees. Another 7am flight, this time only getting me into Newark, but at a good enough hour to get back to work the next day. For those who have more experience travelling than I do, how'd I do?

Also, Of the sites that I used (looked on filtering sites like priceline, but booked all through the airlines' own sites), American was the only one that allowed a 24 hour hold on the seat without having to pay immediately. I thought that was good.