Understanding my bill after switching to unlimited &more

That is not a bill.  It’s a customer service summary.  

My customer service summary says my bill is going to be $199   See photos.

my bill is not $199, it’s $168.  Taxes are always screwed up on the summary. 

1. First of all, in the prorated column, why would I be charged a savings discount for each line after switching plans? Perhaps the -$93.33 is suppose to offset these charges? Either way… if the two plans are comparable, how would a prorated price leave me paying 32.68 more on top of another plan? Your new plan apparently started several days into your billing month and you were previously billed $100 for Mobile Share Value. The -$93.33 is the credit for unused days of that old plan. The $70 charge covers those days with the new plan. Same thing with line charges.
2. If this the first column prorated, why would I pay the full $70 service fee for my old plan and the full $75 for the new plan? The $70 is partial charge for the previous month. The $75 is the full month charge. That is what the new plan will be every month going forward. These two are not prorated and instead are totaled in the last column despite being almost entirely through the end of the month.
3. The unlimited (new) plan was advertised as $145 or $49/line before taxes for 3 lines. I’ve signed up for paperless billing and autopay so how can this be $230 even with the installments I have remaining. This is the column that should be showing less than or equal to my old plan at $215/month. Your paperless billing/autopay discount is not there yet. It takes 2 to 3 bill cycles to show up. This is also your service summary, not the actual bill. Your actual bill might be different.

By the way, once the autopay and multiline discounts show up, your new plan should be the same as your old plan. Three lines on your old Mobile Share Value should be $145 also ($100 + 3 x $15).