Some great ideas here. I would also encourage using priceline/hotwire/entertainment rate as your primary method, and then, when it makes sense financially, work in these options:

(1) Get a Priority Club and/or Marriott credit card - their sign up bonuses seem to yield the most valuable results. If you could get both, you'd have enough points for at least 7 nights in decent hotels plus two free night certificates.

(2) Make sure you stay enough each quarter to maximize the promotions each program offers. For example, if you could book two cheap weekend stays at a lower Marriott brand (like a Fairfield), you get back a free night cert. With Priority Club, if you register for enough promos, your first stay could easily earn you back a free night. There's also a $75 rebate on weekend stays right now.

Use (1) and (2) only when they are more cost-effective than using an opaque site or in the rare instance where precise location/cancellation matters.

(Also, always give your loyalty program number at check in on priceline stays. Often you'll get credit anyway.)

Would be great if you would report back and let us know how it all plays out.