Supplemental income will get you through lean times—and you may discover that you really like working in the wholesale space, too.

Supplement it with some business / legal classes, Spanish (if you plan on being around construction), take some real estate classes if offered as electives and you should be all set.

Talk to the home inspector ahead of time, ensure they are unbiased and will provide supplemental photos/videos of the property.

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. 

Other tenants are highly allergic, as am I. 

My ex-roommate hates cats and is slightly allergic so would always keep the door shut.

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