My plan is to supplement that with a business focused in helping local people in California get access to the great rental market in Baltimore, either through direct ownership or debt.

You are look way below the Middlesex County limits.I totally understand not wanting roommates, however, the ability to supplement even a condo with roommates can be phenomenal and an easy way to get started in RE investing.You final question has a few concepts packed together:1. -$100 a month does give you some tax losses plus the depreciation.

Aggressively paying down the mortgage by supplementing the 500$ in cash flow with an additional $1,000 in personal income we would pay the mortgage of in approx. 10 years and save more than 120K in interest payments.

Long term, I would like to just keep buying and holding, I would like my W2 job to be a supplemental income with my real focus being in real estate, and if I do decide to quit my job, that will hopefully be a realistic option on the table. 

The best time to make big changes is immediately, supplementing your tenants rent when below market is charity not business.

I wanted to supplement my reading with other sources of information, which lead me to the Bigger Pockets podcast.

I'm very OCD and like order so the night before I try to have all my clothes/supplements ready and gym packed.Non training days: Caffiene/Nootropics and cardio by 6 am.Rest of the morning is getting ready for work by 8 am. 

Being an agent can be good supplemental income on the side if you do through commissions.

@james masotti  It's so funny that you say that because we were just talking about the market turn yesterday at my local reia meeting and I was explaining like it is at  Its peak and about to turn so my plan is to flip this particular property as soon as possible just to create enough capital to then invest in a multi families because at least by doing that Having flow every month it will supplement the Down turn Because in my market that's pretty much what does make sense And yes it's a pretty nice area but I gotta say the deal is good due to the fact that we got a distressed property owner so it almost just fell into our laps 98 % hard work and positivity 2 % luck lol 

I have also been working part-time as a server in a restaurant to supplement my income.