Just did one this morning, and it was smooth as silk...
I responded to a "points for transfer" thread on the R/T board...the other owner recognized my screen name, and I recognized his, so we started out with a certain level of "comfort" in dealing with each other...both of us have lots of posts (I have over 1000 and he has almost 1000)--
I volunteered to send a check, and wait for it to clear, before we actually did the transfer...he suggested PayPal, but I despise PayPal and basically refuse to use it...
So, I mailed the check--he called me when the check arrived and told me he'd decided he could trust me and we could go ahead and schedule the transfer before waiting for it to clear...(we did a fair amount of chatting with each other, first online and then on the phone, as we figured out how we wanted to 'do the deal' so more comfort with dealing each other developed over the course of those communications...)
As it turned out, our schedules didn't mesh til this morning, and by that time the check had cleared...
We did a 3-way call this morning (not because I didn't trust him...in fact, I gave him my member number "just in case" something went screwy w/the 3-way call)...
It took a bit of time--maybe 10 minutes, by the time MS finished checking that this was his one transfer per use year, and my one transfer per use year...and MS asked both of us for our member numbers, and the last four digits of our SSs--whether they would have needed mine had I not been on the call I don't know...likely not, but they did ask me for mine when it came time to get my member number and designate which of my multiple contracts the points were going in to...
I wanted to be on the call because transferred points don't show up online, and I wanted that "surety" that the points actually went into my account...
Easy-peasy...
The only "hard part" will be determining your comfort level (you and the other party to the transfer) on "who goes first"--payment or transfer. Someone just about has to "go first" because points transfers are final transactions--so either they have to be transferred prior to payment (even w/PayPal there is a small time lag), or you have to pay prior to transfer.
Dealing with someone I "recognized" from DisBoards gave me the comfort level I needed to go forward--but I knew I was taking a risk, and chose to proceed anyway...
I'm delighted with the transaction...really like the owner I got the points from, and really wanted those extra points, too (w/out having to add on--and I'm already "borrowed out")...
Now, of course, I have to call MS to use them, since transferred points don't show up online...and I think it was DebandBill in a recent thread who pointed out that not all MS CMs are "good" at dealing w/transferred points--and I found that to be true the one other time I transferred points into my contract...but I think if I "keep it simple;" i.e., use all the points for my next reservation (that won't be a problem--grin!) prior to using any of my own points that do show up online, I ought to be fine...and I'm keeping the confirmation number from the points transfer "just in case!"...
Good luck w/whatever you decide to do...