Tips on Buying Cars: Trading in Upside Down van, honda suv, taxable benefit

Question
I am an active duty Marine currently serving overseas and looking to get rid of our 2000 Town and Country Limited AWD.  We have been paying just under $500/month and started paying in Sept 03 and have a 60 month loan.  Interestingly, this vehicle has been a disappointing lemon with mechanical problems.  I guestimate that we are about $5000 upside down with what we owe (or something close to it) to what it is worth.  It has about 68,000 miles and in good to excellent condition.  I have been contemplating trading it in for a Toyota or Honda SUV (something that can hold a family of 5).  What is the best strategy for being able to finance something that we can have for year ahead?  Is it possible (or good financial management) to lease a vehicle for a few years at the same monthly payment of $500 to get my wife and kids a good mechanical vehicle while I am away again that I don't have to worry about?  The lease would allow us to maintain our monthly budget, allow us to pay off the upside down amount and bring us to zero in say 36 months to start over or even keep the vehicle (if we like it?)  Or is purchasing a new vehicle a possibility?  I am up for any suggestions.  Semper Fidelis.

Mike

Answer
Hi Mike
Lets consider both options - Leasing VS Financing...please copy/paste my website into Google
http://usedcartips.bravehost.com/index.html
and click on BEFORE YOU SHOP it will give you a better understanding what your dealing with and from there feel free to ask more questions
Most people lease as it becomes a taxable benefit - does this apply in your case ?
Financing the Dealer should be able to roll the negative equity into payments,the key here is to stay within your budget
You will find buying import VS domestic more expensive,again does this extra cost fit the budget...
Here are some questions i need answering to help you further
your Zip Code
how many miles a year average
Where you thinking $ 500.mth leasing and paying off the Approx $ 5000.seperate or did you mean having everything included in the $500. payments
You also must shop your trade at more than one Dealer,we will get into that area if your interested...
A large portion of e-mail through allexperts becomes an open window for all to view,if you decide to reply then lets keep it personal e-mail me at paulsenray@yahoo.com
Regards
 Ray