Transaction costs in both your strategies will eat you alive. The time horizon sounds long but is actually short. No one knows where the market will be in 3 years or 8 years. It could double, it could tank. You're trying to fast track equity/savings by letting others pay down your debt. The best way to do this through real estate on a relatively short time horizon is to go for a 15 year mortgage. If you put 20% down on a 300,000 property, assuming a 3% interest rate and 4% annual appreciation (which is simply throwing a dart but based on historical appreciation rates), in 8 years you will sell for $410,000. Subtract 6% for transaction costs and $125,000 for the remaining mortgage debt, that leaves you with $260,000 in equity on your $60,000 down payment + call it another 10k in closing costs. That's close to a 17% annual return. Not bad.
BUT, again, these are a lot of assumptions. Can you actually break even on a unit with a 15 year mortgage, association fees, and maintenance? (Yes, its a condo, but water heaters still break, assessments are real, etc.) Can you carry the unit if there is a vacancy? Will you have the money to fix it if a tenant trashes the place? Also, you truly do not know where the market will be. If there is no appreciation whatsoever and you sell for $300,000, you still walk away from closing with $156,000, but that 4.7% annual return doesn't look nearly as appealing for the amount of work and risk. And there is always the possibility, as many learned a decade ago, that you could have to sell for less than you bought it for.
Look at Mr. Money Mustache, Dough Roller, Money for the Rest of Us. Take a hard look at your spending habits. Create a savings goal, enact painful budget cuts, and if you still cant hit the number you need 8 years after these calculations, then maybe real estate is worth the calculated risk.