They are no different than an owner occupant, beyond their monthly payment going to a landlord instead of a bank. 

if there are a lot of houses with a converted garage in the area you won't have any problem but if there is no or almost no conversions, converting it back to a garage may increase your ARV more than an extra bedroom does.

But then you have to deal with payments and accounting yourself.I would NEVER EVER purchase a property outside Chicago, and even more than an hour from where I live.

It was great for income and all our guests were great, but it did get a little exhausting for us.

Just looking for all the options I can exhaust.

It's still better than an individual.Now, Matthew, you seem to have the experience.

Any advice would be greatly appreciated.426.530 Right of redemption -- Manner of redeeming -- Purchaser to receive writ of possession and deed. (1) If real property sold in pursuance of a judgment or order of a court, other than an execution, does not bring two-thirds (2/3) of its appraised value, the defendant and his or her representatives may redeem it within six (6) months from the day of sale, by paying the original purchase money and ten percent (10%) per annum interest thereon, and any reasonable costs incurred by the purchaser after the sale for maintenance or repair of the property, including but not limited to utility expenses, insurance, association fees, taxes, and the costs to conform the property to the minimum standards of local nuisance code provisions and other local ordinances as authorized in KRS 65.8801 to 65.8839. (2) The defendant shall pay the redemption money to the clerk of the court in which the judgment was rendered or the order of sale was made.

I have some substantial loss carryforwards and at the current rate it will take me a few years to exhaust them.

I would like to stay in Manhattan or the more desirable parts of Brooklyn if I can find something I could affordable and worth my time, but would be open to other options as long as they are no further than an hour away from Midtown.

It will be fine to sign a single showing agreement to that particular buyer he is bringing rather than an exclusive multiple listing agreement which will be for a certain time period and you will not have the right to sell by yourself.