Advice on replacing vs painting siding

[Kate Zolov]

Hi everyone! 

I'm Kate and I'm honored to be part of your community. BP inspired me to start investing in RE in 2017. Since that time, me and my husband bought our first live-in-flip. We've finished all the work inside the house. And we stuck with the siding. 

The house is located in blue collar neighborhood, the properties around our house have new (good looking) siding, but ours definitely in a bad shape, has dark color, was painted by previous owners. It was poorly made, since a lot of j channels are missing. So we decided to replace siding , we got permit. But yesterday, after watching BP show 399, where Jeff told about painting aluminum (the one we have) siding instead of replacing for vinyl, we started to question our decision. 

If some of you could give us your .02 about it, I would appreciate. 

Do you think replacing would give us better ROI? Does it make sense to paint over painted siding? We're going to perform the most work ourselves, so in terms of money we are looking ate $1500 for replacing vs $600 for repainting, plus the time we put in it.

Thank you! Attaching some pics for better understanding.