2008 Limited with about 64k miles

In the last two months I have had the same intermittent issue present itself.

After driving 20-30 minutes (in cold weather), shutting down the car, and then trying to start it up about 5-10 minutes later, its cranking and failing to start. Try again a few times..when it finally catches its a very rough idle for about 5 seconds before it settles and then its normal and drives normal. I am finding it difficult to service the issue because it does not happen often but I can tell something is eventually going to go..

I did new spark plugs in Sept 2016 at 48k miles. I put in a brand new battery in early 2017 at 52k miles. I replace and/or clean the air filter often as well.

My suspect area is probably something fuel related. I've never replaced the fuel filter/fuel pump. Where is the fuel filter located on the 08 Liberty and do you think this is the correct area to start my troubleshooting?

I think that you may be on the right track with something fuel related. You may want to use the Schrader valve on your fuel rail on the passenger's side of the engine compartment and see if it is maintaining pressure after the engine is shut off. Take the valve's cap off and press the valve, holding a rag over the valve opening to catch any fuel spray if there is pressure. It sounds as if you may not have pressure in the fuel rail, making it hard to start. One check for this is when starting the engine, turn the key to the on position first. You should hear the fuel pump in the tank kick on. Leave the key in ON for a second or two, then attempt to start the engine. This should build pressure in the fuel rail and make it easier to start. Why you would lose pressure, if this is the case, I don't know. I'm sure that there are check valves located somewhere in the fuel line to maintain pressure, but don't know where it/they would be. You should of course check for leaks at any of the fittings along the fuel line from the tank to make sure you're not losing pressure that way. Leaving the key in the ON position to keep the fuel pressure built up then crawling underneath to investigate should do the trick. If you don't find (see/smell) any fuel leak, I'm guessing that a check valve or the fuel pump is the culprit.

It doesn't sound like the vehicle is operated regularly (only 64K on an '08), which could be a big problem, depending what type of fuel you buy. If you are in an area requiring gasoline additives such as MTBE, combined with an ethanol 10% mix, that can wreak havoc with fuel left sitting for a couple of months, even if you are using something like Stabil. This type of fuel can damage lots of engine fuel system components if it is just left stagnant for long periods of time. If you are forced to park the vehicle for more than a week or two at a time, recommend finding a source in your area for non-ethanol fuel. This, when combined with a good fuel stabilizer, can keep fresh for a few months.

Awesome, appreciate it.

Do you know where the fuel filter is located on the Liberty, is it inside the tank as part of the fuel pump assembly or located outside the tank?