Second, I choose properties that will command a high enough nightly rate.

It would be a challenge to take much of a pay cut, and with my lack of experience I'm not sure I would be able to command the same level of salary  I do now.

The apartments need minor improvements to command at least $100-$150 raise in rent once the current leases are up.Like I said before I just want it to be fair for everyone.

@Patrick Senas , in order to command top rent, your unit needs to be top-rate.

Might not hurt to get an opinion from the Metro area command on the effect of such business activity on the neighborhood, too - which leads to ...My next thought is inadvertently turning the neighborhood into  a 'hood by encouraging unsupervised congregation around your (unmanned) vending machines with no way to police or otherwise control participant activities.  

I find myself wanting to sell and take the large equity amount into another muti family property, but just as im most likey going to get top dollar the new property i buy will probably command top dollar as well.I guess my question is being that i lived there for about 4 year im being told i wouldnt have to pay much taxes unless i net over 500,000 jointly with my wife.

We exposed the brick, refinished the floors, did a drop ceiling  and added new electric, comm and hvac.  

@Jared Bouzek , that would definitely help out, but I would not be able to command that large of a purchase on my own right now.  

The south suburbs have mostly SFR that are also dependent on Section 8 tenants, but command high rents.  

After the necessary fixes it looks like this property just won't command that much in rent so I'm considering looking elsewhere.