We originally didn't accept section 8 or housing tenants, but are reconsidering because the property has yet to be rented.

Initially he had many complaints about the unit and I sent him an email asking if he would like to reconsider renting the unit, given his obvious displeasure (thus giving him an out before officially signing the lease).

If you need to rely on any degree of luck to get descent tenants that will pay on time and not destroy the property you might want to reconsider because luck does not work in this business.

Which is great if you aim to be a "casual investor" that wants the "buy it now" version of real estate (which if you are, you might want to reconsider RE :) ).

So the market has slowed down compared to the past 1) May want to reconsider how much you are charging, as others have suggested. 2) Check out this thread. 

Great discussion here - definitely reconsidering my initial position.

I know I would have to pay Capital Gains Taxes on it so that's really whats making me reconsider.

Otherwise, reconsider purchasing. 

You do not need to give a specific reason for doing this, just let them know that at the end of x month that they will no longer be able to live there....However, if this tenant has been; long term, hassle free, and prompt with their payments, maybe you need to reconsider moving them out as you may find the loss in this cash flow to put a hurt on your income.I would say a good compromise would be to see if the tenants want to upgrade to the bigger unit, where you being the kind landlord offer a "reduced" price to them.Ultimately it is your decision, but be sure that your decision is not based on emotions but rather simple dollars and sense. 

Hi Samantha, I'd encourage you to reconsider requiring cash/check.