Does anyone have any experience or advice on PM software that can handle vacation rentals as well as yearly lease rentals, storage units, etc?  

I have a different insurance company handling each state. 

Anything smaller reduces that chance.  

If the seller would pay a huge tax burden, seller financing can reduce it by spreading it out over years instead of the one-time hit. 

If your managing your own properties that you have a clear ownership interest in .. no licesne requiredif your managing properties for your clients IE collecting rent.. negoatiating leases etc.. then yes you need a brokers license with a PM component.. and you would have to work for a broker for 2 years then sit for your principal broker exam pass that and the property manager component..does not matter resi or commercial.. reason is your handling lots of money for investors and or negotiating contracts state wants those folks to be licensed and accountable. 

City services, which primarily depend on tax revenues, will be reduced.

One lesson I learned as I started my investing business is that this is not a task that one can handle alone.

They may not be large enough to handle large repairs, or even have the resources of people to call for this type of work.

Unfortunately I am still paying a reduced monthly rate.  

Exchanges work well for moving up to a bigger unit but they do not work if your goal is to reduce debt or take cash out.