Over time, as you get exposed to more circumstances and situations your judgement should improve and you should rely less on the 'rules'.

My wife and I listed last week, the home is over-improved for the area, so we knew we may get a lot of activity.  

Property values increase when neighborhoods improve.

I'll make improvements over that time and hopefully sell it for a profit or a least break even.  

Lets add in the improvements.....Adding $10k per unit would be $30k and your return on investment for the improvements made will most likely be too low for it to make financial sense.

I have been hesitant to rent out my current home because we've spent the last 5 years remodeling and improving the home to such a degree that, with it being in "move-in ready condition", I would be worried about how renters would take care of it from here on out. 

Turns out she didn't completely chase me off with a shotgun or anything, but she did tell me that if her situation doesn't improve, she'll definitely be calling me to discuss more details.

But probably not if you don't think it would improve the property.

I have taken great strides in improving my credit recently, and have also looked into what it will cost to start up a LLC.

Keep a good part of your focus on the rent you can achieve with the improvements you're making.