Ok I did a quick run through of parts on advance auto parts site. It puts you at ~$140 in parts to replace everything back there on your 7.5", that is assuming that you have 10" drums. You likely have 9" but the price is close to the same, maybe a little less. I'm sure you could beat that price if you shop around, and I know you can do the work yourself if you care to try. The hardest part of working on drum brakes is adjusting them and bleeding the system when replacing a wheel cylinder.
Now the 8.8 is likely to need the same work done. If you go with a bolt in Ranger 8.8 with drum brakes you are looking at about the same price for parts. If you can afford it I recommend go ahead and do the swap now, rather than having to buy the parts all over again later. Better to spend 300 now than 140 now, plus the 300 later when you do the swap.
As others mentioned if you are going to do an 8.8 swap you might as well go with the Explorer disk brake axle. Especially if you can weld (or know someone) and if they are really the same price as you suggest. Given your desire to lift and run bigger tires the disks would be a really good upgrade. New pads and rotors will run you 100 bucks, give or take 20 depending on which pads you want. Disks are a lot easier to replace. You biggest drawback to an explorer axle will be installation, you have to flip the mounting brackets (welding), figure out shock mounting (potential welding), and figure out how to hook up the parking brake.
If you know you want an 8.8, you don't mind drum brakes, don't mind spending the 300 (including new brake components), and don't want the hassles of installing an Explorer axle I recommend go ahead and do the swap. If you want the 8.8 disks but can't handle the mods required to mount it I recommend doing the brake job on the 7.5 and save up for the work needed to mount that axle. If you want the 8.8 with disks and can handle doing the swap now I recommend going straight to it.
You have to do some welding on the axle tho. If you dont know how to do brakes, I highly doubt you could manage to make the professional welds needed for this swap to work smoothly.
I think that's taking it a little far. Knowing how to weld and being mechanically inclined are completely unrelated. I went to school (avaition maintenance tech) that could weld great, but were not worth a crap at most things mechanical. I now work with a few electricians and a number of sheetmetal (basically a body man for aircraft) mechanics that are great in their respective skills, can weld good, but once you ask them to use more than remove a bolt they are lost. On the flip side I can do almost anything mechanical that is needed on one of these trucks from brake jobs to engine rebuilds, but I can't weld (though I've only tried with stick). To quote my welding instructor from school "thank god (I) only have to be able to identify a good weld, cause (I) can't weld for shit." He also said that he was sure he could teach me to weld better, but I'd have to sign up for classes cause there wasn't enough time in that one.