If you are you will be successful if not you will learn quickly that it would be a waste of money to invest in training.

If you have questions related to financing/ mortgages feel free to contact me at your convenience & I'm always happy to help as this is my specialty

With experience, you will find some values that don't scale and will know how much to adjust for, but minus that experience, think of rules of thumb like training wheels. 

Should I just 'tell our rental story' and how we've used that as 'training' for the next investment?

Go to their training sessions. 

My main goal right now is to learn the business, I’m not sure which of these two would be a better on the job training/experience for me.

the reason that lenders generaly do not go that low.. is you simply cannot make enough money on the file to make it worth the time or risk.when I had my HML company it was my specialty but I had flat fee of 3 to 5k per file.. so its hard to advertise your charging 10 to 15 points.. but when you quantify that to dollars its just a few grand on these small deals.. and if your deal craters.. the HML put out 30k to make say 2 or 3 points that's not even 1k.. and the cost of foreclosure would be far above that.. and the HML would lose their butt on those deals.. 

Now I need live training to assist an investor as I learn.

If you are ready to learn from the people around you and work hard, I would suggest not shelling out 20k on the real estate training courses out there.

If you don't know what notes are or want to do the work yourself, I highly recommend signing up on their web sites for free training.