Welcome to the best thread on the DIS!!
Well there is a lot to digest here - but what an AWESOME plan you have this summer!
First off - before you get too excited on the mortgage piece, there are fees to do this and depending on your mortgage company and other factors only certain cards may work. I'm not the expert on that, so I'll leave it to others...
The "change name" benefit on the CP is a nice feature, but it's good you're pretty much set on your son as your companion. You can't "hold" flights for future companions (i.e. you can only have companion flights booked for your current companion) so switching a lot on short notice isn't a great idea.
Your plan could burn through a lot of SW pts quickly (which isn't bad - just be aware of that). You'll need to each fly separately somewhere to meet up, then fly somewhere together. 30,000 SW pts is worth about $444 in flights (and he has his $400 credit). You could spend all of that just on your "meet-up" flights and now all the additional travel ends up being out of pocket... Maybe you should consider earning some more SW points real quick...Do you have a side hustle (sell items on ebay, teach piano, sell cookies, mow lawns, consulting, babysitting, etc.?) You could qualify for the SW business card which would earn you another 60k SW pts for just $3k spend. Here's some thoughts on this plan:
- You should already have 34k SW pts (30k + 4k base pts)
- This would earn you 63k SW pts (60k + 3k base pts)
- A SW BIZ would be the absolute IDEAL next move for you IMO if you want to have enough SW pts to make your summer travel dream a reality without spending a ton of money.
- Now you have enough for $1,400 in flights which could make these dreams a reality
- ADDITIONALLY - you have 97k SW pts earned this year...if you earn 110k SW pts in this calendar year...you could get that CP to carryover into 2020!!
- How do you earn the add'l 13k? Well you could start by referring your boyfriend or your son to the SW personal card - that would get you 10k pts. Would one of them consider signing up to help you out? (Of course they'd get a bunch of points out of that too). Then, depending on how much you spent over the MSR on your bonuses you should have less than 3k pts left. Maybe spend another 3k on that card (OR I could give you a hit on how to use a refundable flight to make that happen!!)
- You could also transfer Chase Ultimate Rewards (URs) to Southwest BUT those don't help you earn a CP for 2020 so that would be a last resort strategy - vs. what I listed above which is GOLD!
Now your other problem is obviously hotels - this one isn't an easy answer. Hyatt, Hilton, Marriott, IHG - they all have hotel cards. Chase Ultimate Rewards can be used to book hotels and transfer to hotel partners.
- Hyatt & IHG have limited earning opportunities since they have minimal cards.
- Marriott has a lot of ways to earn but numerous restrictions around which cards you can apply for if you held other cards.
- Hilton has a ton of earning opportunities but if you abuse AMEX you can get shutoff from future cards with them.
- (This game really is fun - I promise!)
- You could go with Chase Ultimate Rewards (there are 7 cards in total that earn URs) and these can be used on hotels through their Expedia portal OR transferred to Hyatt for a good value (or Marriott for a meh value).
- URs would be an especially good strategy if you are open to business cards as there's 3 GREAT ones there.
- However, picking a hotel chain and signing up for their specific cards may not be a bad plan either. The thing URs provides is flexibility though, and since you're going to numerous cities (potentially over 2 years now) picking one hotel chain may not be your best play. (Due to prices, availability of rooms, etc.)
Hopefully this helps and doesn't further confuse - ask questions! I'll also send you a PM invite to our private reddit group DISchurners where we have more info and you can potentially support other DISers when you apply!