1990 Jeep having cranking issues
 

My jeep (1990 Cherokee Laredo) has started having to turn over five or six times before it actually cranks. So, where as a normal jeep goes "chug chug chug VROOM!" my jeep is going "chug chug chug chug chug chug chug chug VROOM!". I can hold the key in the full tuned position, let it chug about ten times, then it cranks, or i can try to crank it, stop, wait 30 sec, then try again and it cranks normally. Is this just an old jeep quirk or is my car about to explode? :confused:

could be any number of things, my advice to you is to first check the spark plugs as they could be fouled, and chuck some injector cleaner through the engine.

For starting issues. I always start with the basics. Clean battery terminals. Contacts on the starter. Main Ground. If it is distributor, check points and cap. Plugs and wires if electronic ignition. Voltage on battery, coil. Keep it simple first. And Good luck!

Any difference when warm vs. cold? Is it better if you recently shut down?

If temperature makes a difference I'd look at the coil or crank position sensor. If you need a place to start then the coil's much easier to get to.

If it's a first start of the day thing then I'd check the fuel system. (How long since filter was changed?) Get a pressure gauge (~$25) and test at the fuel rail valve. Should be ~31psi idle, ~41 peak. At key on it should jump to 8-15 for the ECU prime then up to normal once started. Problems can be at the filter, regulator, or pump. If you want to cheat, have someone kink the return line before you turn the key. If it fires more quickly than normal you're closer to knowing the problem.

Useless nitpick: if you're describing symptoms to the shop then cranking and turning over are essentially the same thing. Turning over often implies at least partial ignition but it's ambiguous. Remember the origin of "cranking" is from using a handle out the front of the engine. "Firing" obviously indicates some kind of air/fuel ignition.

K.I.S.S.
First, check the battery and cables. Next, a tune-up and filters. Then check the fuel sytem, sensors, etc.
16 model years... how many miles? Without information on your maintenance and driving habits, we have to keep our advice rather generic.
Have fun!