I can't answer all your questions, but I have started transfering some of my domains to my Supersite account at Directi and have not had any problems with the process. I think you do have the same 60-day hold with them as you do with Godaddy, who told me it's an ICANN rule and not a Godaddy rule...
I think domains do get slapped with a ad-infested page when they expire, but I was surprised that I was able to get some domains transfered out while expired, so that was a plesant surprise (I didn't allow enough time for the transfer to complete).
It's nice to know the PayPal deductions are normal, but those considering becoming resellers will be paying a fee when they transfer money into their PayPal account, AND a fee when someone pays them via PayPal! So if your prices are too low, you may not make anything. Then you are faced with how to price things so you can make some money, but also not scare off customers.
I have found it difficult to communicate with their support, but they are helpful and have called me directly as a result of an email I sent. This last time I wrote about the PP fees and also that while they tell you HOW to set up things like slab pricing, they tell you NOTHING about how this can affect things. Is one slab too few? Are 10 slabs too many? How should you set the pricing? Well, the answer is, it's all up to you...!
There are a lot of "traps" for new resellers, even those with experience (I'm a 56 yo Internet consultant). I looked around the system to find out how to replace the "your brand" logo with my own. I checked templates and settings, and looked though HTML code for headers and could not find it. During this last call I was walked through some steps where we created a new tempoary template. THEN one of the images was available that I will be able to replace with my logo.
It's a powerful system with a lot of features and options, but it's not friendly or well-documented as you work with it. They DO provide a lot of videos and help information, but there is so much to learn that it would be more helpful to include it in the system itself.
I think they need a user's group of some kind...