Just for posterity, I applied to about ten residencies for rotations from late march to early april. I sent love letters to ones I liked the most, and got 4 approved by the end of april. 3 thru VSAs, one thru the program.
I also have one program that I am waiting to see if they will take me early 2020, but I am not holding my breath.
My general advice: if a program doesnt take you in 2-3weeks they probably will not. Keep applying, the longest a rotation took to accept me is 3 weeks anything longer than that has basically rejected or ghosted me. Apply to all tiers cause it will surprise you how some low will reject you when higher ones don't.
If one rotation rejects try and get another at the same instituion if possible when you really want a place. I got my final rotation by emailing after getting rejected from two different services. They told me what was left and thankfully took me.
The other thing. This stuff costs money, and none of the rotations I have aren't helping with housing. And most of them have some extra 75-150 fee beyond VSAs, even if you use the no fee feature. So plan on paying $15 to apply plus that fee. It can add up quick.
You can apply for multiple months for no extra fee as longas its the same rotation with the same service. I havent had much luck with this, as the ones I did it for basically ghosted me, but its an option.
I would expect to pay $600 to $1000 for housing from rotating room or the local contacts these places have.
The academic places can have some LOOONGGG charting training they make you do online ahead of the rotations. I had one place that required over 5 hours of 'interactive' videos that could not be sped up. Pretty much pure torture.
Programs also open at different times on VSAs, alot of people told me to apply early but most programs I was looking at didnt even allow apps till march 31st. Surgery seems to open earlier tho.
Also you need to get a copy of your LOR for whatever specialty you are interested in. Many programs have started requiring that this year, as well as letters of intent. Some places want a personal statement as well. And I uploaded my CV to everything.
Basically have your whole app ready by march of third year and then you can get aways in early 4th. It sucks, but thats how it is for us.