Really, my interest in having an upstairs apartment would be to rent to family, but I don't want to make a terrible investment decision.

I don't think I will be looking in DC more like the Alexandria, Springfield, or Woodbridge unless that's all considered part of the larger DC area I am not terribly familiar with how everything is referenced.

@Chris Seveney that would be a slightly...terrible.

Being as my bills are not terribly high probably around 2500 a month (but with little savings) Would it be wise for me to pursue a real estate career or maybe something along the lines of a carpenter or in the trade of fixing up houses?

Carpets are terrible for people with allergies too. 

Mike Mike , check out Keith Weinhold’s recent podcast on “Why Home Equity Is A Terrible Investment.”

Cleveland isn't a terrible area but there probably aren't any true "A" properties in Cleveland.

But that does not look terrible.

What are some platforms you have had successes, and failing that, terrible experiences with so far?

If you're considering doing business with someone that you aren't sure of their legitimacy, you're making a terrible mistake.