Just started with a new employer that pays for housing, vehicle, and fuel.

Are you only referring to damages in excess of the deposit?

I'm not so worried about "anonymity" because the house is our primary residence, so we're not hiding, but we want to look like we don't have excess assets.  

Any cash flow in excess is gravy (on the poutine, I would guess).

Don't know about anyone else, but I feel like my personal daily battle is between doing what is urgent and fuels my raging undiagnosed ADHD, or what is actually important.I've done a ton of work on this over the past almost 4 years, and still am nowhere that I think I need to be, but I'm at least getting to a level of awareness I don't think I ever had before and that is a win in my book.  

In the last month and half, I've been working supporting a local real estate investor, which only goes to fuel my passion for getting into this business. 

Hi Kyle, 1500-2000 is excessive.

Rent control measures, burdensome employment regulations, and excessive administrative requirements exemplify this.

Other then that use excess money to do pay off CC and then do a BRRR/Flip a couple times

Even the $85 per yard mow seems excessive.