If you're talking about your parents retirement money, I would go the safest route possible and divide that money between a few different experienced operators syndications / funds.

Start at home, do the maintenance work in your home, if something is broken and needs to be fix try to do it yourself before your parents call for a trade to have it fix .

As you've already discovered, dealing with their cosigner can also create a lot of extra work and come with problems, particularly if you have a helicopter parent or two.Home care for four residents?

Hello all, we have had a family cabin near Long Barn for a few years and I'm about ready to STR it to help my parents out with the overhead.

Now the landlord has to eat the cost of the attorney, it took a month or two longer, probably will raise rents, screen harder and ultimately the vast majority of good tenants get to pay the price.That's why I donate my time to the RPA Rental Property Association of Wisconsin, which is a local non-profit REIA and we lobby in Madison for sustainable landlord tenant laws - if you are a Wisconsin investor, please consider joining.

I honestly wish my parents and I had been knowledgeable about real estate when I was going to school and would have loved to do this. 

It was enforceable by any property owner in the community since it was a restriction on the parent property.

My parents are putting me in charge of the entire investing process because they're too far retired to want to deal with it, so naturally I want to make sure I'm making the best decision for all of us. 

If you are interested in real estate investing, have one of your parents take you to a local real estate meetup and talk to some investors.

There were a few slight distractions like figuring out financing, selling a neighboring lot (that I had also acquired via letter writing) on Craigslist, rent out my RV, rent out my house, make my first ever documentary film (a twenty minute short called Kara, Star Of The World about a woman with a traumatic brain injury from a childhood ski accident), take any photo and video work I could get, start a 360 photography company, create social media channels to hype the build, parent two small kids, do a beautiful and excruciating tandem mountain bike ride across Scotland, drive my family on RV trips to Colorado/Arizona/Utah/Nevada/California/Wisconsin/Minnesota/Michigan/Florida, attempt to write a novel and adopt a puppy.The above may read as humble brag, it is not.