Milan or Rome airport?

Where will you be visiting prior to your departure? Do you know which rental company you'll be using, and have you checked their weekend hours?

After both arriving and and leaving from MXP last month, in my my mind, it far surpasses FCO. It is now my preferred airport for Italy. It is now a world class airport since it's updating over the lst couple of years. FCO has a long way to go to catch up.
I've peen "repping" an Italian company for the last 3 years and have used both FCO and MXP depending on the cost and convience of the flights, however, I do my best to avoid FCO because of the chaos and employee attitude at FCO. Also, in my experience, the hotel rates at MXP are much cheaper than around FCO.

I flew into MXP in June for a 10 day vacation. It was truly carefree. I had only a large backpack (no checked baggage) and I arrived about 8am on a Sunday morning. I completely walked from the gate and out the door in about 5 minutes. Walked through customs, no lines, etc.

Then...within another 5 minute walk, I found the train to Milano Centrale. The train is about 45-50 minutes to get to the main station. Then we took the fast train off to Venice.

The nice thing....after our 10 day vacation, we returned back to Milan and took the regional train up to Verenna on Lake Como for a nice, low-key day. After 10 days of crowds, cities and travel...the slow day on Lake Como was great. For us, it was a day trip from Milan...then back to a hotel near MXP.

It worked out great.

normally price of the flights would dictate what airport you land or take off from. Usually flights into Milan are cheaper.

From nyc during peak season, Milan can be half the price vs Rome.

Price is not the issue since we are using miles and at this time reward flights are available from both Milan and Rome. The only issue is the ease of dropping off the car at the airport and finding suitable lodging nearby. We had a problem years ago trying to drop off a rental car in Florence because they closed Sat. afternoon and all day Sunday. My understanding is that the airport rental companies will be open 24/7. Am I correct?
What car companies do you recommend? We will be picking up a car in Venice (Mestre?) and driving it in Italy for 2 weeks. Would love to save a few bucks but am mainly concerned about dealing with a reputable company (local offices).

You can drop the car off right by the terminal at MXP and walk to the check-in counter.

Unless my trip was staring in Rome or south, my choice would also be Milan / MXP. I find it an easier airport to get around, as most flights arrive at T1 so only one terminal (easyJet and some of the budget carriers use T2). The transportation options from T1 are good using the Malpensa Express, about 52 minutes to Milano Centrale and about 40 minutes to Milano Cadorna.

I used to think I'd rather fly into Roma but I used Malpensa last Spring and will again next month. Rates are usually better for flights to Milano, and it's so easy to get to a train and off to where you're headed.

Last year I stayed at a B&B in Milano the night before. This time I'm passing on that.

By the way, http://www.trenord.it/EN/ is the site to use to purchase tickets between Centrale and Malpensa in advance online if you need to. Trenitalia shows their schedule but doesn't allow any purchase online which I thought was strange. I then learned from a Trip Advisor comment about TrenOrd. It was good for me because I return to Centrale on the earliest train from Firenze and have 10 minutes to locate and board the train to the airport. Rather than risk missing the train to the airport because I can't purchase a ticket at the station quickly enough, I purchased it online already and have no worries about missing the train. That will give me nearly 2 hours to catch a Delta flight.

If you want to use the Italo train, you can take the train from Malpensa to one of the Milano stations Italo uses. I'm trying it next month for my initial jaunt to Firenze before heading to southern Tuscany.

You can also take the bus but as a photographer, I no longer wish to store all my gear in the busses belly during the ride. Taking the train I can keep it with me.

Since you are flying on a mileage award and therefore price isn't an issue, you should base your decision strictly on your overall itinerary. If your itinerary includes Milan or surroundings (e.g. Lake Maggiore) then Malpensa makes sense. But if your itinerary includes Rome and you don't care to see the Milan area then you should use FCO. Malpensa is more modern and less chaotic than Rome, but if you are not visiting anything there, it's a long way to go. Also MXP is far in the middle of nowhere so it takes longer to reach the morning of departure.