If you go too big 4-5 bed it may appeal to a multi-family setup but those are few and far.

If you did choose to do it now you could possibly never have to change it out again during your holding period and you could boost curb appeal in the process. 

With home prices being higher right now, at least in the market that I'm located in it seems appealing.

@Maureen SepulvedaHi Maureen,I've seen similar shingles roofs repainted (over the original stain) and from the road they look interesting, but up close if the shingles are past their service life the paint doesn't hide that fact very well.Maybe beige walls and dark brown shingles would make it look more appealing?

A lot of the areas too like Raleigh/Durham also keep making the very desirable places to live lists, so that's appealing as well.  

But I see potential pros like easier rental short-term and potentially more appeal/demand from student renters who are only around for say, a semester or two.

Some VC money / investors are leaving and startups are not as appealing here as they use to be, but established tech companies are not going anywhere.

Curb appeal is huge.

I want to appeal the tripling of the assessment for 2020 and thought an accountant's certification on the form TC309 would help my case.

For example, painting the exterior of a building might not seem like a value add because residents live inside but it's major curb appeal and it increases the volume of resident tours/applications thus allowing for a rent premium.