I agree with @Steve Vaughan - don't bother painting the trim. You can get wood stain repair sticks that are like a pencil for small repairs. To me it sounds like you are putting a lot more into a rental rehab than you need to. I live in a pretty nice middle class house/neighborhood and my trim isn't caulked... I could easily rent it for $1500+
I would have your painter guy do the hard stuff - ceilings, cabinets if you really need to. If the color isn't offensive and there aren't stains, why paint the ceilings (eg the bedroom you referenced)? And why are you painting the garage ceiling???! I wouldn't even do that on a flip unless it was stained badly.
Paint the cabinets if you really think you need to, but be really careful with painting the trim. Sometimes it works great, sometimes not. I had a (skilled/experienced) painter friend do it in a place I'm just finishing up and wish I would have just replaced it. The stained wood just didn't take the paint well in some places even with good prep work and a quality primer. Sure we could have sanded it all down, but labor gets expensive fast and you probably have to take it off and reinstall it anyway to do that. I will probably be replacing it all over the next few years now anyway. So, if you just want white trim, it's probably a lot cheaper to replace it (and the doors) - buy the pre-primed stuff, paint it and install. Plus you have brand new trim.
Also, if you have a decent handyman, have him paint the walls - he probably won't do as good of a job as the great painters, but it will be 1/2 the cost, and should be plenty good for a rental. It shouldn't take him more than a couple hours to paint a room on average, $25/hr + paint should be just under $100/room.
I bet you can get your painting bill down around $2-3k, maybe $4k if you do the cabinets. You might get $25-50/mo less, but it takes a long time to recover $4k+ in cashflow. Maybe consider doing this work in phases if you have a vacancy after a few years.