I know most will suggest not painting brick but I don’t think pant removal is in the budget and when I look at the side not painted already, I’m not impressed with the appearance of the brick.Also, it is on a dead end street in a rural area with about 10 other brick ranches (none painted) and I think a stylish gray with matching new roof will make it stand out.  

What questions do you ask to figure out if they will be a good match, and what do you learn from their response?

There are banks that offer matching when you're saving for your downpayment too such as M and T (up to about 7500 I believe). 

Many homeowners in the surrounding neighborhoods rent their entire houses for football and graduation weekends, and other big events like exhibition matches with Manchester United, etc.

Do I HAVE to pay for the second garage door ‘just so they match’??

You guys might be a good match!

As for the unit freezing up; I am a HVAC contractor and if the unit is installed with a blower size that matches the evaporator coil the unit will never freeze up.

My contractor is recommending the house be resided with some T-111 because the bottom part of the siding, about knee height and down has some rot and he doesn't think we can find the same style siding to match.

White is easiest to match, goes with everything, easiest to keep looking good, and is interchangeable with other rental units if necessary.

I do have an employer match, which I’ve lowered my contribution to meet the max employer match %.