If you hold for more than 1 year as a rental, then you sold, you would pay short term capital gains taxes at 15%.So your intent and your actions dictate if you will pay ordinary income + self employed, or if you will pay long term, or short term capital gains.

Like every other city, there are market specifics to each that may dictate whether a property is a good deal or not, the potential for appreciation, and the quality of tenants you might get.Good luck!

Similar to what others have mentioned I believe there's many different factors that dictate a persons living situation.

Your state code probably dictates that this means it goes MTM.  

The timing of their paychecks dictates how they pay and they are living hand to mouth- they don't have enough savings to pay when they should and don't have the discipline to start saving. 

This element ultimately dictates the ddesirability of the business and therefor its price.

However, if you don't dictate how they find the deals or make it mandatory to see where they have driven, then there are many bird dogs out there willing to provide deals for some type of finders fee.

How much capital you have will dictate investment options to some degree.

@Paul Tibok, technically only a lawyer can dictate the specific wording for you, or if you are using a Realtor that person can write it into the contract, although it doesn't have to be complicated at all. 

This will be dictated in how long it will take you to find a new tenant and the now 'tenant(s)' would be responsible for rent up to and including the start of the new lease however, I don't believe you can charge for anything that would have fallen outside of the lease in any instance.