I am a financial independence "enthusiast" if you will and always interested in adding more semi-"passive" incomes streams to supplement my current investment portfolio (mainly index funds at the moment).

If you are unwilling to supplement the condo until rents appreciate enough to provide positive cash flow then the decision is obvious. 

I’m going to flip houses to supplement my income from being an agent and looking to use 100% of my flip profits to buy rental property.

I am working on making this something to supplement my retirement and pass on to my kids to continue.

I've been toying with the idea of getting into rentals as some more supplemental income, and although I've struggled with the math as far as justification, i believe the main reasons folks here by rentals (please correct if I'm wrong) are: Cashflow (although I've seen people do deals eg on Roofstock for only $100-200/mo) + appreciation (when sold) + taxesSo assuming I'm correct there, then the potential tax benefits are 30% of the reason to do rentals.

No place in my business plans for supplementing tenants rent when taking on inherited tenants.

Continue to immerse yourself in education, listen to every podcast with supplemental reading.

If you buy right and manage right you can absolutely be profitable and supplement your income with one property.

Some day I will need to step out of public schools (I teach shop, so I like hands on work) and I'd love to have real estate supplement my income. 

After talking to a few people about thier friends that started real estate investing in the same position as i am, most of them used credit to start off until they aquired the capital where they didnt need it anymore, or it was more of a supplement.