This is what good brokers do all day long, outbound on 5, 6, and 7 figure names. When all is said and done, it's just sales.
If you believe in the product you're selling, then sales is easy. If you're trying to swindle a crap name on somebody for $300, then the low price doesn't make it easier. Crap is crap.
It's the same amount of work to prospect, contact, and attempt to sell a $1,000 and a $100,000 name (same amount of work, not necessarily the same amount of skill)
In fact, brokers only work with higher tier names because the commission on a 6 figure name makes it worth their time. While a commission on a $1,000 is peanuts and would bring shame to their families.
The question is if any "investors" have done this, and the answer is yes, of course.