How do I plan TOC/TOD in an IFR flight plan that includes SIDs and STARs? For a checkride, I'm being asked to plan an IFR cross-country from Miami Executive (KTMB) to Tampa International (KTPA), using SIDs, STARs and approaches.

I'm going to use MIA5.MIA (Miami Five Departure) to depart KTMB, then get radar vectors to the WINCO transition, then fly via V97 to LBV (La-Belle VOR) and then use LBV.BRDGE8 STAR (LBV, ROGAN, BRDGE, JSTRM, PIE), and then get radar vectors to the Final Approach Course and perform the approach at KTPA.

My question is, when choosing the fixes for the flight log how should I include Top Of Climb (TOC) and Top of Descent (TOD)?

For the SID, which one of these options should I use:

1) Write KTMB, TOC, DHP, WINCO
2) Write KTMB, TOC1, DHP, TOC2, WINCO

Option #2 has two TOCs because the SID states that I should maintain 2,000 or assigned higher altitude, and then expect my filed altitude 10 minutes after departure.

And then on the STAR, where should I place the TOD: after the LBV VOR or after ROGAN? And what altitudes should I write after LBV if I don't get a descend via clearance?
I'm not sure if there's a standard, 'correct' way to do this, but for planning purposes I'd just assume that your climb and descent aren't affected by the SID and STAR. Calculate them as if it were a VFR flight, in other words, based on the route you have.

The issue here is that you don't know what ATC is going to do. The SID says "maintain 2000 or assigned higher altitude" so it's possible that they just clear you directly to your cruising altitude. Or they might keep you lower for a while for traffic, or have you climb in multiple steps, or whatever. Unless you know the local ATC practices very well you can't plan accurately for that and even if you do know what altitude they assign 99% of the time, your flight might still end up in the 1% that gets other instructions. Ultimately, you have to deal with whatever ATC gives you.

It would be worth asking your instructor about this too. First, he may have a better answer than I do! Second, he may know what the local ATC procedures are in that area. And finally, since you mentioned a checkride he might have some insider knowledge on what the examiner expects or likes to see. However you end up planning it, you should be able to explain to the examiner how ATC's instructions might affect your time/fuel calculations.