I don't fly all that much, nor do I stay at hotels all that often. All my travel is for leisure. I'll take, oh, ten roundtrips and have five or six hotel stays during the year. Here are a couple of the most important rules I've devised for myself so far:
1. Try to get points for as many things as you can. I'll get E-Rewards and MyPoints for some (limited) "bonus" points, but I always make sure to have a reward credit card and use it to buy as much as possible. (Pay it off every month, though!)
2. Limit yourself to one or two reward programs. For example, I have both the HHonors AmEx and Visa. I use the AmEx everywhere I can -- 3 points per dollar spent. My wife also has the AAdvantage Mastercard, so we pick up some miles there. Having the credit cards is key -- they enable you to collect a serious number of points/miles for doing nothing other than living your everyday life.
3. Pick a hotel program and use it for your stays, even if they're infrequent. The same thing goes for airlines -- I pick one to fly with most of the time, so I can build up maximum miles with them.
4. When you reach that glorious point of actually being able to book a reward -- don't use it for something that doesn't cost very much. For example, I fly Southwest HOU-DAL quite frequently, but I won't ever use a free ticket for that. I'll use it, for example, when I'm flying HOU-SMF for vacation in wine country.
Sorry to go on for so long. But I'll close with this: The first step, which FTers are so good about reminding folks, is to pick your program. It sounds like WN would be a good choice for your airline. They have great service out of BWI and terrific fares from there, too. Next, pick a hotel program, if you so desire. Then decide which credit card will work best for you.
For me, my most costly travel expense is a hotel. I'm based out of HOU/IAH, and I prefer Southwest. I can usually find a really cheap ticket to fly where I need to go, so the flight costs are pretty manageable. But if I want to go on vacation for a week, I'll need to drop $1,000 or more on the hotel. So I chose to put my credit cards with Hilton. I've racked up a ton of points doing that. And now I've got eight free nights coming up in Napa Valley and Sonoma County this summer -- which would have cost me about $1,350 if I had just paid the lowest available rate. I've got a RR ticket on Southwest to get me there -- thanks to those somewhat frequent HOU-DAL trips. But I'm paying for my own rental car -- why? It costs 70,000 HHonors points. I can get a full-size car out of SFM for $200 for the eight day period. Not a judicious use of points.
So that, in a rather large nutshell, is how this on FTer does it. I don't travel as much compared to many on this board, but this is what works for me. Hopefully you can find something useful in it. No matter what, it's just fun to gather up as many points as you can!