Facing a dilemma! What to do? Pics of mine

[Kaysenmc]

Need opinions from people with the same feelings for their trucks as I do.. I have an 86 K5 lifted (see sig and pic) and I am considering selling it.
The story..
I built it pretty much ground up about 3 years ago got laid off january of 2009 and sold it (for $6500) to pay bills. I got back on my feet and got another toy, then traded that truck back for my blazer (which has now been beat down pretty bad). I have it almost squared away but for it to be the ultimate blazer I have always wanted, it really needs about 3 thousand put in it. Needless to say I like my blazer as is even though its kind of pointless to have due to having several others and it gets pretty poor mileage.
When I sold it to the guy who was hard on it, a second guy really wanted to buy it but couldn't get the money together fast enough. Well now that I have the blazer again, the second guy called and has cash and is ready to buy it for real this time!! (only 5500 this time though)
Whats everyones opinion?

I'll still have my 87 swb, and a 2006 chevy swb that I consider my daily and also my rallye 350 for the car show/fundrags season.
I better add that as of Jan 22 I am engaged and plan to be married August 21 this year (everyones invited), so we are in the process of doing all that fun wedding stuff plus in the middle of buying some land (house, water, septic, and electricity too).
I guess I just feel that since I have very little money in the blazer it would give us a good start on life together (she also has an 89 k5 that she drives daily).

So anyone with any constructive criticism or comments would be appreciated, as I have really been thinking and worrying about what to do.
Thanks in advance everyone and heres some pics!