Welcome to the Board! Remember, 300,000 HHonors points is "only" $150,000 worth of spending on your Hilton AmEx card.
Also, watch for promotions (extra points for buying gas and groceries, etc). You can convert "stray" miles from several airlines (DL, CO, TW, UA, MX, to name a few) into HHonors points. Also, you can apply for a "mutual fund" HHonors account so your husband's "stray" miles can be converted into it too.
E-Trade offers up to 50,000 HHonors points for opening up an account with them, so if trading stocks is in your blood, you can get points (and miles) to come with it.
Good luck!