Mine is 96

 

I did exhaust, cams, tuner & dyno time on my 96 last winter. Now I regret not doing 110 kit for the money I have in it now.
It feels like spending $$$ on these things never ends.

 

I look at it as

You need exhaust. Period.

You can get a cam like the 555 for now and do 110 later. When you do that you can get it cheaper since you won't have to get cams, rods, lifters, etc. Plus it will be an easy swap.

Depending on cam choice they all are needed to work together so it's not really a waste

 

More displacement doesn't get you much unless you up the compression. Then you're also looking at different cams that are more aggressive like the TW 888 . It also adds a lot of labor for not much gain. Maybe do it if you do the heads and are upping the compression, but once again that is a different cam.
My 2 cents, labor, pushrods, and gaskets for a cam swap is usually between $500 and $600. If their quoted price is all labor then they are overcharging you.
If you have a ThunderMax and they are not a ThunderMax tuner then you shouldn't be paying them for a tune as they won't be tuning it. For the tune I suggest finding a map or asking TMax for a base map that matches your new setup and then let autotune do it's thing. I had to manually adjust timing a bit with my Thundermax as well but you've already paid for a lifetime of tuning by getting the ThunderMax. Don't let them touch it.
Do the 222 cams with the pushrods and save the exhaust money to see if you want more power. If you do then do the big bore, up the compression, put in different cams, and replace the exhaust. You will already have the tools to replace the cam and can sell the old one with very little money lost. Stepping through the stages has opened my eyes to the cost of upgrades as compared to the actual gains. Cams and exhaust are the cheapest and you already have a bit better than stock exhaust that gets you around 20% gains. Once you start doing big bore with higher compression and a more aggressive cam and 2 into 1 exhaust you are talking big money (around 4-5x as much) with only 30-40% gains. So $600 for 20% gain or $2500 for up to 40% gain. And those are costs for doing it yourself. I don't want to know what all that would cost at a mechanic or dealer.

 

I was thinking that going to a 103 kit may be the biggest bang for the buck. Not as much as power as a 110, but not nearly as expensive. Can you get more compression in any of the 103 kits or is it all same standard compression?