If a m2m tenant won't complete required leases or other paperwork in a timely manner, I increase the rent each month until they decide to be reasonable (it hasn't take long in all cases)

Initially intended as a long term hold How did you find this deal and how did you negotiate it?

I have a side by side duplex I have been house hacking for the last 4 years and I am unsure if I should keep it or sell it.

Yes they can do averages based on what they saw on the last three remodels. but have zero clue as to the little nuances that pop up on every job.I would find a good General Contractor and pay him to help you with this.

After years of sort of cruising on auto-pilot with a single tenant on a long-term lease, we figure it's time to assess the real value of this longtime family investment in case it might be time to sell.

Initially intended as a long term hold How did you find this deal and how did you negotiate it?

It will take a long time to recoup the cost on a property this size. 

Yes, most of our DSCR products do NOT have pre-payment penalties (as long as you are not refinancing AND had the house on the market in the last 6 months) and with 20% down would be the in mid's 7's assuming good credit/DSCR over 1.00 etc. 

On REOs, HUDs, VAs and other you can get inside but most of the time the utilities are shut off, and heat has been off for a long time at least one winter, in some cases more than one winter and are possible freeze damage to water pipes, hot water heat pipes and even boilers/hotwater heaters. 

I don't know how long it would take and I'm not even sure I would get a response so I could be wasting time.