Prioritizing upgrades and execution strategies

[Allison O.]

I purchased a small house last fall. I could see myself living there for a few more years, but things could change and I could also need a bigger space. Either way, I would keep the property as a rental. I am also working towards getting my first rental property next year. 

My current home definitely needs exterior updates for curb appeal. Sherwin Williams did a free exterior paint consult which was great, but now I run into execution. I got a few quotes from $1500-over 2k to detail paint the windows, gutters, siding above my porch, the railing, and shutters. And if I do this myself, it would be tedious and not guaranteed to look great. The windows, doors, gutters, shutters, and porch railing could all stand to be replaced. If I hire a local contractor that would be affordable, they will expect me to know exactly what I want (I have an idea but need guidance). If I go to a design and build, they will have the vision I lack but be much more expensive. I don't want to pour money into this place if the ROI doesn't make sense. Another option is to do one replacement at a time, but I want a cohesive end result and doesn't want to stretch this out for years.

So, what would you spend money on and prioritize? Are the new things I listed above worth it? Or should I just take a chance and paint everything and see what happens? Picture of the house is attached for reference; the first picture is what is currently is and the second is a rough rendering of what Sherwin Williams suggested I do.

Thanks!