If he stays anyway, most leases have a punitive holdover clause that would charge him bucket of money because he is injuring not on your property but also the incoming resident. 

I understand there is also property management software that combines ACH payment capabilities with feature with basic book keeping features, perhaps work orders/repair requests, document(lease) archives, leasing/listing features? 

My investment goals include building a portfolio of rental properties, focusing on both single-family homes and multi-family units.

Do you own any properties yet?

Yes, they made me the property manager.

We've bought over half of our properties during the holidays.

By investing out-of-state, you can find properties with lower prices and higher rental yields.

Also as a sidenote I assume you are lending on non owner occupied homes - never lend on an owner occupied property.

I currently have a property with a 4 unit on it.

Any other strategies for using 1031 money in this situation or is it only for purchase of a new rental property?