Welcome to FT!

To answer your questions...

1. It doesn't really matter, but since you're transferring, it's usually easier to have all the miles in one account so you don't have lots of orphan miles spread across several accounts. It's also easier to book two tickets from one account rather than book one, then another, hoping availability is still there.

2. I suggest you look at the UA rewards chart. You have 85,000 miles once you transfer your UR points, meaning you can get two return tickets of 42,500 each. This gets you two return tickets to anywhere in the continental US, Caribbean, Mexico, Central America, and Northern South America at the Saver level. To get to Hawaii you'll need 5,000 more miles, which shouldn't be to difficult. Saver rewards are a bit harder to come by so you need to be flexible with dates and/or check regularly. Your SAS miles won't do you any good. You have too few and can't pool them anyway, and you certainly can't transfer them to UA.

http://mileageplusupdates.com/images...ward-Chart.pdf