It can be harder in colder parts of the country but not impossible.Just last week I found 2 tenants- one for a C property and a 2yr lease for an A property.I did reduce rent by $50 and scheduled 3 showings at the same time for the C prop.

Not the best scenario, but they deal with your creditors, reducing the rates, and you will be paid off in 5 years or less.

Because they want to sign for 5 years, which will reduce vacancy costs, I should probably reduce the annual rent increases but I have no rule of thumb to go by. 

Why would a savvy RE investor in his final days write a 5 year lease for one property that reduces rental income and/or the ability to sell for his sole heir?  

I remember reading a blog post a few months back that someone had written about using a third party website that helped reduce their vacancy rate significantly because it would reduce pricing to entice more people to possibly choose your rental.

Retail customers are typically scared by the foundation repairs as they are very costly, but I have a couple of big investors who salivate every time they see a foundation problem - it is fixable 99% of the time, and that also means a big discount, since the seller knows how it affects the sale and has no choice but to reduce the price. 

The accountant cant also apply property depreciation to reduce your taxable income further that I for the life of me cannot compute on my own.If you don't use software, hold onto all receipts related to rental property and calculate at end of year, but really you would benefit from implementing a system early like quicken that you can grow to help you track multiple properties when you get to that point and categorize everything and assign the expense to each property so your end of year organization becomes something simple like handing over the schedule-E forms to your accountant.

I'd also talk to a lender to see what loan options I have and what I need to do to get better terms (i.e. increase credit score, reduce debt, etc)

So I could reduce the rent by $100 or re-list the property and sit around for another month.

Rather, they will increase as the value of a dollar is reduced.