I want to one day be a big lender, funding deals and pursuing my career in music / speaking.

Investors profit with Principals on the deal...that's how it works, but if your "Teachers Union" investors are simply owning stock market shares in the company on the stock exchange they are "Playing the Market" up and downs and are not sharing in the profits of the company.

@Kay Kay Singh Glad that worked out for you, but IMO that's playing with fire. 

You want to minimize the chance of being without a chair if the music stops (and having to chase the market down to sell).If you don't have a lot of experience rehabbing, which it didn't sound like you do, then I'd say it's safer to stick to a smaller rehab.

Should I get my license to level the playing field?

I took a pay cut with my company to keep it afloat, play the long-term game, and to stay with the company/help it grow, so I have been strapped with cash.How should I responsibly handle this 1k/month once we move in?

Plus, I didn’t play soccer in 2nd grade...but nice guess.

Obviously also the amount of leverage plays a large role.

Play them accordingly.

Corona Virus just dropped Canada's prime rate at 0.5%.. it will definitely play a roll on travellers moving around..