We used the lease option strategy so we would buy properties under market value and we would keep them for only around 3-5 years and then we would sell them and trade them up for more properties with the equity that was created.

Have proof on hand (easy enough to find) online of the missed tax payments and any documentation that supports that he specifically didn't pay his taxes.Probably a simply mistake on his part, but now if he wants to develop on it, he either has to land lease it from you or buy it back.I'm not sure how the whole tax deed thing works, so that would be something you have to figure out between the two of you.

But once I got the bills, I increased the rent with the tenant's approval and signed an addendum to the lease stating the rent increase would be X and the owner would take over utilities.

And each year when the lease comes up for renewal, I ask them to contact the housing authority and ask for a rent increase.

All this in addition to 6 other lease violations... 

Out of 4 tenants, only one has abided by the lease. 

With this route you can purchase a turn key property and expect to lease the property immediately or purchase an existing rental from an investor that doesn't require rehab and has strong numbers. 

@Tamika Davis One of the biggest advantages of most software on the market is to complete these tasks you mention (maintenance, leases, rent collection, etc). 

Managing from afar can be done on single family homes with a few properties, but you'll still need a solid leasing agent and handyman which can sometimes be hard to find. 

I think the folks trying to do Airbnb and short term leasing in Cleveland's many Section 8 neighborhoods are out of their minds.