I apologize if you explained this in another post but when are your stays and how far apart are they? Did your second window open and also since you did get through, what solutions did they offer you. Did they book your fastpasses for you manually if you were not able to do it yourself?
I am local and basically we went to DW every weekend in March. Stays were Friday through Sunday or just Saturday night. We stayed a combo of DS, SOG, and actual Disney hotels. Since getting our AP at Christmas we've been 11 over night stays. I have run the gamut of holding 15 fp at one time to being locked at 7 with remaining other on site days that could potentially have fp. I currently have a Saturday night stay at Coronado in late April, a weekend stay at Hilton Palace, a Saturday stay at the B, and a long weekend stay club level at BWI all for May. I was able to get a combination of "multiple experience" fp (not valid for TSL or Pandora) for a couple of days and time specific non-modifiable fp for the other days and "all day" ride specific ones because half my family already had fp made. I spent multiple hours on the phone with multiple CMs.
I at one point had the two May stays at DS hotels windows open (blue and clickable), but couldn't make fp due to the 7 limit. Then they disappeared. The stays remained on MDE, but are not blue on the fp calendar. I was able to piggyback or umbrella under my dh and 2 kids for the early May Hilton Palace stay and get fp for myself and other 2 kids. I never could get the B Saturday night to open and there wan't anyone to piggy back for that one. The email to Kalogridis helped with getting fp for that date.
At this point, I have become frustrated with a very lackluster Caribbean beach stay, paying to park at the resorts (I know, not a new thing, but it still doesn't sit well with me), and the whole 7 day limit when I pay to stay on site and can't access that benefit. Also, I did some "experiments" with morning emh and regular entry. It was basically the same, other than losing the hour and maybe one ride. Don't get me wrong, I LOVE emh. It's a great benefit. We take full advantage of it and get there early. I can see the writing on the wall though, and as my kids get older it will harder to drag them out. That said, I have some of my BEST disney memories at a 7 am MK emh. I would purposefully stay on property to take advantage of 7 am emh.
While growing frustrated with those things, I also got much better at scoring FP last minute. This, along with the 4 kids getting bigger and Disney rooms being small or TWO being even more expensive and the laundry list of other things, has led me to research off site places. We have a stay first weekend in June in a 2 bedroom resort west of Disney. We love Disney. I've been going for 40 years. I've brought 6 month old babies and 4 kids by myself prior to even living in Florida. We've been on 3 disney cruises. But the things are adding up. I am excited to see SWL, I can't wait for the BatB sing along, GoG (even though I haven't seen any of those movies) looks amazing, etc. We will still go, but as life changes and Disney keeps increasing costs (restaurants and room rates) and fees (ie, parking charge at hotels...I can totally see this at deluxes, but WHY for the values and mods), our method of visiting will change. We are lucky to live close. We go a lot and I still plan on going a lot. Where we stay and how much we get nickel and dimed will determine how much on site we do. AND how they fix this. If I am limited to 7 on or off site without a major hassle of phone calls, why would I pay extra to stay on site?