Every property comes with its own characteristics and challenges. we have sold to hundreds of investors by now and there are some that had a bad experience as far as the property goes but theres also tons who havent had any issues.

Challenges?

It has brought me into a great depression mentally as I have to start all over... but its hard talking and trusting people now.

The more challenging stipulation is you would need to use it more than 50% of the time for business use (and you need to log the miles to document that).  

Being young will present challenges in a field where experience is highly valued not just with lenders.

That process has direct lender involvement.Where the challenge lies, is when unsophisticated "investors" with no experience, no money and no reserves use creative financing (often called wrap, subto, lease option, seller financing, land contract) to purchase properties and along the way there is a "hiccup".

Your situation sounds challenging. 

Avoid common pitfalls like underestimating costs or tenant management challenges by planning conservatively and staying proactive.

What are the biggest challenges people have faced with this.

While I own quite a few rental units already, I thought condos might be a good option to gift to my kids when they turn 18, offering them a safe introduction to property ownership without too much risk.However, my challenge with investment condos is that the cash flow always seems terrible.