It's not that easy to accomplish and usually involves advanced strategies such as bonus depreciation mentioned by @Logan Allec and asset segregation.The good part is that investor-friendly lenders will add back depreciation, not counting it against your income for underwriting purposes.

Not to mention you need to bump up your vacancy to 5% or greater.

@Blair Poelman mentioned that the dry cleaner business might throw up a red flag.  

I had two "aha"moments early in my career and I believe I have mentioned them in previous posts.

My question: do I send a general letter simply stating that I'm interested in purchasing the property & request that he call, or do I mention the tax delinquency & let him know that I'd like to help him solve this problem.

It was just the holding deposit document which said mentioned my move in date and gave details of the rent in case I sign the lease.  

@Terrence Williams  As you mentioned, most of the specifics will come out during each individual deal, but I think you're generally asking the right questions for this kind of preliminary meeting. 

This doesn't sound like it's a "private money" deal since you mentioned a lender and fees.Private money is cash you get through friends, family, etc.Are you referring to a hard money loan?

And since they usually have big riding mowers, it takes 15 minutes to mow the lawn.However, you do mention that your landlord friends have guys that are cheaper.

So, learn about that first - and a good point to start is a Nolo book (https://www.amazon.com/Every-Landlords-Property-Protection-Guide/dp/1413307000/) mentioned in the doc, it will explain about insurance, how to evaluate insurance, and then about property management, property code, proper leasing and all the way to LLC and hiring.