WE painted our cherry veneer 20 year old cabinets in our old house. We also replaced appliances, counter, backsplash, fixtures and found the old floor. I think you are on the right track removing the overhang, but also removing the soffit will make a huge differnce. Do it if there is nothing in it that is too difficult to relocate. If you do not replace doors, definitely fill in the groove and sand flat. You also be able to add glass to a few uppers to really make an impact. The fun thing about painting old cabinets is that you are not destroying anything and making an improvement. You could try different colors. We pained ours about every 3 years, first white, blue, then yellow. I wanted to try gray but we sold the house. We also cut out some of the uppers for glass, but ended up cheaping out and using wire. We also used Soapstone remnants, since we did not want to tear out anything too great because we wanted to eventually replace cabinets (moved first). We were able to them for $2500. Before: First remodel in progress (no finished photos): Yellow:

My wife worked as a Home Depot paint department supervisor and said the Glidden Gripper was the primer they recommended most of the time mainly because no one seemed to come back and complain about it. She said personally she would go to a dedicated paint store, not a box store. Prep is important especially when painting over wood previously stained and top coated as you have experienced first hand. It's going to be tough to find any coating that can withstand the wrath a vacuum cleaner, but you can be successful with the right products. I perhaps take an overkill approach but I would sand, vacuum and tack cloth everything, clean with TSP and mineral spirits, then use a liquid sandpaper, then prime with the best primer you can find and finally paint with the best wall and trim coating you can afford using the best recommended brush you can find. It's a lot of work and maybe a step or two more than needed. The TSP and liquid sandpaper are maybe overkill but that's what I would do.

Unfortunately I can not tell what colors , I used Photoshop. But what I read from Photoshop... You might want to try River Blue by BM or Dark Harbor BM

Thank you for the suggestions @ decoenthusiaste, @ Momofthree Ma and @ Beth H. We are on a limited budget, so we won't be able to replace the siding. Do either of you have suggestions on the best way to add window trim? Will we need to have someone remove part of the siding and re-flash the windows to do this Also, do you have any suggestions for what we could do with the steps? We don't have a budget to build a porch, but could make some minor mods to this structure. We will be adding some landscaping this fall.