On second look, that fuzzy-looking dead leaflet in the last photo might be botrytis/grey mold. If you have other brown, velvety-looking lesions on your plant, you might have a grey mold problem, which can also attack flowers. Botrytis lesions can form v's at leaf tips like verticilium. In dry conditions, it can be less fuzzy and look like early blight.

Thanks gorbelly, ill try to get some better pics tomorrow! So bt if its pin worms and ik theres nothing i can do for vert. The reason I suspected vert is because an infected branch was hollow when I trimmed it off.

at this point though it's so late in the season i might not even treat it.

Hollow stem is more likely something other than verticillium, especially higher up on the plant. Maybe pith necrosis. Could even involve a stem borer? Unless your plant looks poorly all over, I would not suspect verticillium. If it's just some leaf lesions and flower drop, it's probably something else. Note that some pests can also be another of the many, many possible causes of flower drop.

I think it's more likely to be any number of fungal or bacterial diseases that attack stems than a soil/crown disease like verticillium. Possibilities include: bacterial stem canker, alternaria stem canker, stem rot, grey mold, etc. Many of these can cause parts of stalks to become hollow. I would personally try to treat with aggressive pruning of affected parts, spritzing some diluted bleach spray on lesions on areas I can't prune off, and then spraying fungicide. At this point of the year in MI, I would concentrate more on getting already existing fruit to maturity than about setting new fruit (except for cherry plants). A beefsteak size tomato needs a good month and a half to two months to become a ripe fruit. With declining temps and less sunlight, that timeline gets stretched out even further.

Maybe someone with a more discerning eye can chime in with a clearer diagnosis. And I know Seysonn makes successful use of a bleach spray to control grey mold. Maybe he can offer some advice.

Note the classic tomato pinworm hole in the left-hand fruit in the last pic.

Yeah I'm with you I don't think its vert at this point either but I agree the new fruit really arent too much of a concern for me at this point. I already have more tomatoes then we could ever eat anyways better not get greedy haha