I have tried to get her into a duplex where she will have rental income to supplement SS but she can't afford a mortgage.

My goal in real estate is to supplement my income and eventually (in about 15 years) replace my day job - I love what I do but I do not want to be hurting like the old-timers I work with now.  

They may already be supplementing the parents in this case anyway.

I work full time in IT and I am looking to supplement my income with real estate, specifically buy and hold.

I want to establish an income stream to provide a supplement in case my next posting isn't as lucrative as this one.

It's certainly not necessary but it can give you a bit of an edge.If you're thinking you can get licensed and start doing rentals or sales to supplement your income, I can tell you that it's WAY harder than you think.

I do you currently work for someone as a subcontractor but I am trying to supplement my income with getting my own work whenever possible to help increase my capital for investing in the future :)

There are those who simply want a little supplemental income who tend to have inconsistent revenue because they don't really treat it like a business.

I want to own them free and clear to supplement retirement income.

If none tell them you will be raising to market rent but allow them 60 days to move and for you to find better tenants without a vacancy.If you are restricted to $100 then 4 years is way to long to wait to get them to market and you will need to give them both notice to non renew.Assuming you are investing to make money you must make the proper business decisions and frankly giving up thousands of dollars of income by supplementing tenants rents is not the way to do it.