Need some cash to put into the property to attract renters in the shoulder seasons-May and October and November.

It sounds like you have an amazing foundation in place, and a great head on your shoulders.  

The dwarf that sits on the shoulder of a giant can see further than the giant." :)

@Francesco Barbati Sounds like a lot of risk for you to shoulder if you want to do this properly.

Usually where a security is concerned and as so thoroughly explained by Dion, any securities violations would rest on the shoulders of the issuer of that security.

Or, more bluntly, do you want your tenant earning twice as much per month from your property as you, while you shoulder the risk and liability of operating without the necessary licences or insurance and in possible violation of legislation or regulation?

I've found the biggest value from a coaching/mastermind program comes from a few areas specifically:1) Leveraging the network of the mentor and peers2) Having someone to look over your shoulder and avoid costly mistakes3) Accountability (group and individual) 4) Possibly serve as a potential partner on deals I don't think one should have to spend 20K+ to accomplish this, but to each their own. 

For a new agent a 2nd source of income that is flexible and puts you in the same room (or car) as people whom you otherwise would not have met is a perfect recipe for lead generation.Sounds like you have a good head on your shoulders, good luck to you i'm sure you will do great.

During the shoulder seasons things are relatively slow or at much lower rates (besides leaf season for 2 weeks).

Personally if its just how to do a transaction that is what your after just get a real estate license its much cheaper and then go through the training some of the big shops have.. their training is usually free while you have your license hung there.. and you will be rubbing shoulders with people that are actually doing deals.. not people sitting in a cube reading from a script..