I faced numerous hurdles and stressful moments, but I persevered and built a successful approach.To tackle this challenge, I recommend starting early by building relationships and seeking investors.

Here’s my two cents:Paying off the condo might make sense if your main goal is to reduce risk and enjoy the peace of mind that comes with no mortgage.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

I'd also suggest considering a partnership if you feel comfortable with that in order to reduce the risk completely on you. 

There are some benefits to having an LLC on reduced liability, but there are more expenses. 

As Sean above alluded to- never pay a seller for your future hard work, risk and stress. 

ya or older semi retired attorney might be a good fit.. low stress get paid.

This gets them thinking about your eventual move and the stress they might face in finding a new tenant.After some time has passed, you could share that you’ve started looking at other homes, but the options in your price range don’t compare to the property you’re living in.

Step up in basis to reduce your heirs' taxes and morePlus the real estate tax "deferral" can end up being permanent if played correctly

Is there a way to reduce the amount of hours so you have more time for other activities?