I'm looking to do what you have accomplished - get my first duplex and house hack it.

This is my slow part of the year, and I do all the things to move the algorithm…fiddle with order of photos, change seasonality in my photos, tick as many boxes as I can, fiddle with pricing.  

You also must know your numbers and have a real deal.Other reasons may be that the deals presented do not make sense to the lender or you don't have a track record.

If we want to make upgrades to the units while our tenants are in there and negotiate an increase in rent when the lease terminates - suggestions on an appropriate way to do that? 

there are lenders that do land only .. not a lot of them..

And how do you weigh these against interest rates or terms?

I've always been super interested and have helped my mom renovate her place in Bellevue WA last year.

Beyond that you should do a feasibility study.

I bought it for 247K in 2013 and just sold it for 650K two weeks ago with a 1031 exchange getting out of the partnership to go do our own things. 

I would do a video walkthrough as well as host open houses and personally invite the neighbors.This listing has the potential to kickstart your entire career into something extraordinary.