I am needing some advice on what the best choice in my situation might be. I currently have a 2001 3500 Dodge pickup that I use for hauling (170K miles, great for hauling, has air bags, air brake, chip, after market exhaust) and a car that I use as a daily driver. The car has 300k+ miles on it and is about to spit the bit.

I am needing something that is dependable for longer trips that I don’t have to worry about breaking down or if I’m going to make it.. I go through a lot of areas with no cell service and breaking down kind of bothers me…

As far as hauling, I probably won’t be going anywhere other than local/100 mile radius in the next 2-3 years until my son and colts gets older, and if I do go on longer trips I’d most likely hop in with someone.

I am wondering should I :

1. get rid of both and buy a newer pickup and use that as my daily driver and save up for another run around car (super cheap, nothing fancy)
2. keep pickup and buy a newer, dependable car and later on down the road replace the pickup

Any advice is appreciated! I've been thinking this for awhile now and just had to take my car in over the weekend to get something replaced and they reminded me it wont be long....

I would keep your Dodge and get a replacement for your car.  Any time you buy used, you could be buying someone else's headache.  Newer is not always better.  We traded off a pickup with just 22,000 miles on it, because it was a lemon.  Always felt bad for whoever got stuck with it......Moral of the story--low mileage sometimes means it's broke down a lot!  lol

Agree with this advice.  Keep the truck.  Get a dependable driver.

Assuming your Dodge is a Cummins diesel, its barely broke in! (I currently haul with a 1994 Dodge Cummins with 231k miles on it and stick under about 120 miles radius). If it were me, I'd keep the truck and get another jump around town car. That truck will last a long time yet if you keep it maintained. I've grown up around the car business and my brother is a mechanic, and the Cummins (of the age of your's and mine) is the most durable, low maintenance motor out there. 

I LOVED my 2001 Dodge 2500 Cummins 6 spd manual but I needed a 1T so I sadly sold it  - it had less than 130k miles on it in 2017.  The guy who bought it texts me every  so often to tell me how much he loves that truck & so glad I sold it to him.  I'd find a reliable car with good mileage & keep that truck!  

Personally, I'd keep the truck and replace your car. 170k miles is nothing for a diesel. If you maintain it, it'll last a long time! Our truck is 13 yrs old this year with 220k miles and I have no intention of getting rid of it til it's dead. I'd much rather put $1k per year tops, on a bad year, into maintaining an older truck than having a payment of $1k per month on something new. 

Thanks all! Keeping the Dodge is the way I was leaning, honestly, I'd like to keep it forever! Just wish it was a little bigger than an extended cab, that is my only complaint! 

I was in the same position as you:  2000 Dodge truck and a 15 year old Toyota Corolla that I used for grocery trips and running around.  I was fine, I'm not spoiled, all good. 

Then I took my beat up Toyota to a work conference and I was slightly embarrassed to drive that thing.  Then the AC went out.  I am now the proud owner of a brand new Corolla.  I love it, all the fun tech features, great fuel mileage, etc.  So nice.  I always preferred my truck but it's now a bit of a step child.  It will still get me and my horses where we need to go, so I will hang onto it for a while longer.  Also the price tag of a new truck is just crazy!!!

I going to be the odd person out here. We were in a similar position last year.  We had a 2010 GMC Diesel with 60,000 and a Honda  pilot with 210,000 miles. The truck was going to need tires and at the age where things will start to go wrong which aren’t cheap to fix. So we decided to trade in the truck and put money down and purchased a brand new Denali diesel. Our loan payment is actually less then previous and everything is covered under the warranty. I drive the car to take my kids to school and things around town. We drive the truck every where else. I don’t know about you but I don’t want to be broke down with a trailer and horses along the road. 

We we have never owned anything New but this was the right choice for us. We just have more use for a truck then car. Diesels can be expensive but they hold their resell value.

Everything you mentioned is the other side of my delema,  so while looking at cars I've kept my eyes open for the right pickup as well... 

Same here! I have a 2005 Ram 2500 diesel with 240k miles. It's also my daily driver and I'm going to hang onto as long as I can! I'd much rather spend money here and there on repairs than have a crazy expensive truck payment.

We originally started look at new cars but the more we thought about it the truck was more useful and I don’t mind driving a truck when the car takes a crap. Our truck payment is only $538. I refused to have a huge payment, we had to shop around but there are good deals out there and some incentives from the manufacturer. Good Luck!!