However, i would say my best quality is my drive and attention to detail.Some of my passions include ice hockey, fitness, European cars (Audi/VW), and music.  

The car note was paid on time and the rent was paid on time (per both previous landlords).

With the letter negotiating price, you sound like you're selling a car. :-) You'll increase your chance that he'll just move out if you raise the rent an extreme amount.Wording things like "if you had decided to sign a 1 year lease, we would have kept the rent the same," sounds accusing and is a turn-off.Just simply draft a generic letter with a few options.

The guy had a car lot that was getting destroyed.

I've cut back DRASTICALLY on my spending so my only real expense monthly would be my car payment.

Yes, we are regulated to the point of ridiculousness and to the point where it can be cost prohibitive to be compliant but, the protections afforded to the consumer are for the betterment of everyone and, it really weeds out the used car salesmen and boiler room operators that prey on consumers.

Income from your rental should cover that property + some extra, downsize your personal life if you must (pay off car, credit cards, etc).

Do you have a free and clear car?

Once I begin to farm out the property management I would be comfortable with a 2 to 3 hour radius so if I needed to I could take a reasonable day trip to the property by car.

Any apartment complex is going to have a lot of car burglaries, for example, because most of the residents have to park outside.