I’m hoping to have it done and on the market for rent by mid February if possible.Some of my current ideals are Stainless appliancesNew paint on the exterior to really stand out Privacy fence to separate home from ally way that gets a fair amount of walking trafficNew carpet in both bedrooms Possibly new windows as some glass is already broken and they are of original designRe do plants and red mulch with easy to maintain native plants Considering re sealing the driveway and filling in the cracksI’m sure I’m missing a few things, this is a link to the google street view sadly this is the way the home loooked in 2011 and has fallen in a bit of disrepair since.

For homeowners insurance ask if the company utilizes any kind of managed repair program which sounds great but takes a percentage off of material on your estimate,  in my experience this is a red flag and equals a insurance company that will not have your best interests in mind....

He may just be a super successful 23 year old with no friends or family, but it sounds like a lot of potential for red flags. 

Being a landlord is a business it’s not a charity you’re not the Red Cross

@Gabriela Johnson I think there are a couple red flags.

You might not not want to risk having an illiquid investment in the red on your books.But either way, as @Russell Brazil and a few others have pointed out, crowd mentality is fear when there is blood in the streets and normal people cannot pull the trigger in a market flooded with vacant repos.

If you're plan is only to help others once in a while, you'll quickly start to realize that between membership dues (NAR, MLS and local Real Estate membership dues) not to mention monthly office desk fees (regardless of whether or not you work from home) and yearly fees associated with yearly 6 hours of required Continuing Education courses will keep you in the red and start to bleed you dry if you don't have enough business to cover these recurring costs.  

This one immediately puts you in the red on the 1st unit.Are the property taxes accurate? 

Will doing this second deal raise any red flags for me or get me into trouble?

The more you can do to avoid any potential red flags, the better.Property Management OptionsBefore you dive into the rental market, you need a good strategy to manage your rental properties.