@Jason MeadowsMy parents did one over their garage but the structure was there already so it was easier but they still had to go through local permitting and zoning review.

Then you work those leads.When you're done with those...then you are back on the CALL list asking them if they know anyone who might be moving...again you may have to prompt them....who is getting laid off, who is starting new job, who is retiring, who has rental property they're tired of, who should be investing in real estate.When you're done with those, then you start thinking on your own....WHO is motivated to sell....parents who's last kid is graduating from high school, parents who's last kid is graduating from college, people who aren't working any more, people who are going into retirement homes, people who own vacant houses, and on and on.Everyone who gets you a lead #1 gets a hand written thank you card

Income: child support of $1700 a month, $1700 from a job.

I can find a nice house in these places for 300K but probably not the wisest investment and would still eat up a good chunk of my savings for 20%+ down payment.I am newbie and barely contacting lenders and figuring out if I would be qualify for a second home (On Title for my Parent Townhouse) vs. investment property.Just trying to make the smartest move for long term wealth building.

Have a parent-cosign on the mortgage with you.

My parents (who made have a stake in the property) feel strongly that I should hold on to it.

This means that I am living rent free at my parents while collecting $4,000 a month from unemployment.

My parents did this and I was lucky to recognize it at a young age.

My parents wanted a getaway option in winter as well as an area that has more than just a beach (they get bored easily). 

You don't care about moving violations or child support, or even most violent crime (one of the few jobs a felon can get sometimes).