Many of these are conveniently located across the street from the drug dealers.

Commissioner Chloe Eudaly's office has circulated a final draft copy of a renter screening proposal that would take away an apartment owners' right to protect tenants and their families from individuals convicted of felonies and some misdemeanors.Convicted felons and others convicted of misdemeanors would be allowed to rent within three years of the date of sentencing or one year after release from confinement, and include: Drug dealers | Drug manufacturersSex offendersRobbers | BurglarsStalkers

Short term vs. long term is not easy to determine as your might be considered a dealer and income might be ordinary not capital gain.

@Matthew Irish-Jones that's what I figured.

Despite the charming look to the neighborhood there's a heroin dealer across the street.  

It depends on many factors.In general if you are assigning contracts that is a relatively low risk process and an LLC may not be much benefit.Owning property on the other hand is higher risk and I put my properties in an LLC.Mixing the two in one LLC is generally not a good idea and can bring about severe tax consequences if you are determined to be a "Dealer" by the IRS.I am not an attorney of CPA, the above is not to be considered legal or accounting advice for your particular situation but simply how I might handle a similar situation.I recommend Nolo Press, books on LLCs and their webstie as well as seeking advice from a competent professional.Good luck - Ned

It made more financial sense and was much easier than flipping more houses and paying taxes on ordinary income.Makes sense - "tenant" & "frequency" play a key role in being considered a real estate investor vs. dealer for tax treatment.  

Or if you want 4% rules (with some shady tenants like hookers and drug dealers) you could buy in East Cleveland or parts of Toledo!

It's a small neighborhood but I would keep an eye on the Irish Hill area. 

The other thing you need to be careful with in the flipping stuff is being classified as a "dealer".