Hello, I am new here too, and no one has replied to my posts yet (been over a week) so I thought I would say something JIC the same thing was to happen to you.
Pardon the length, but I can talk a lot about stuff that interests me.
They do make spacers that will convert bolt patterns
here are a few:
Wheel Spacers & Adapters : Red Rock 4x4
Spidertrax is the only mfg that i have found that has 5X4.5 to 5X5.5
Yes you will definitly need to lift the jeep to put those tires on.
Stock you can put 30's on, but it may rub a little, and a 3" allows for 31's. For 33's, atleast 5" is recommended, but it would require fender trimming. Personally I think it looks funny to put on 33's without trimming the fenders a bit, becasue the wheel well is too small for it, so it doesn't allow for much upward travel. also the 12.50 width makes those tires stick out more, requiring more trimming (a 9.5" or 10.5" width requires less cutting)
Here is a guide to trimming the wells for 33's (he has 5.5"s lift)
Jeepin.com: Fender trimming your XJ for 33's
I think that getting new gears is recommended to make up for the relative loss of power due to larger tire,and to bring the speedo back to the about right speed, and compensate for any functions that require the vehicles speed, but I am not qualified to elaborate on the specifics.
I also believe that you may want more powerful brakes, so that you can still panic stop okay.
DIY, well, I put on a 2" lift with just a ratchet set, some jack stands and a floor jack. Plus a coil spring compressor and some C clamps. If you have the time and patience you could install a 5", it just has more parts (control arms brake line extensions etc) if you have good instructions and enough sense not to let the jeep fall on you. I would recommend doing it with some pals that are mechanically competent (and if they have nice tools that's good too).
I wouldn't recommend doing any differential work yourself, unless you knew what you were doing.
Trimming is DIYable, and the spacers are as easy as changing a flat.
I wouldn't want to have to trim my fenders, because I have a 01 that I drive everyday, but I wouldn't worry about an 88, the paint is probably not as shiny as mine, just take your time, and remember, they sell replacement parts.
I also recommend sway bar quick disconnects, I made some out of clevis pins and washers for $3
Pic ,
installed (pardon my shoddy welding ability (you don't have to weld them if you don't want to)) its a 2.5 or 3" (cant remember) by 7/16" clevis pin, with 3/8" washers (tighter fit) and a hitch pin, you just remove the old bolt (might be difficult if it is knurled in like mine) and replace it with the clevis pin (note-I kept the original washer too, so it fight tighter) this mod helps the flex alot...
Price:
spacers/adaptors: $200
Lift: 800-2000 (types and qualities vary)
Gears: 200
Total: 1200-2400
(the prices are rough guides, there are so many different brands and types and qualities, hence the wide range of prices)
I think that covers what I have the abilty to cover. GL! I am happy to help with advice (good or otherwise).
stock cherokee new hubs? spacers? lift? 33'' tire help ect. 
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