My life has been turned upside down for 3 months, and you should have approached me about a reduction as soon as you knew the job would be crawling along, and that neither I or any tenant should have to shoulder this ongoing nonsense."  

You'll be able to pull out equity tax free, and then extra tax write offs with the interest paid on the properties.A more conservative approach that I have favored in the past as well is to get a HELOC on the property.

@Juhi Banerjee, appraisers for 2-4 units will use the same valuation methods as a single family home: Sales comparison, Income and Cost approach, with a reconciliation section to account for the variances.  

Now you mentioned boyfriend and not spouse, there are differences for single people and married couples for how much the exemption is under 121, you will want to talk to a CPA to see how you have it set up and how it will apply to your specific situation, but this might be a good approach again depending on what your goals are.Having a rental property is gold in my book.

How old is the property, always an important question in a place where much of the housing stock is approaching 100 years of age?

Or are you more interested in (and willing to) engage in more of a slower, relationship-oriented approach to negotiating? 

It got me so far and I was able to accumulate some MF assets using this approach.

Do you guys have any tips on how to proceed through the agent and structure our approach knowing she was widowed in dec 2020?

And how should I approach it with her?

Do you see any holes in that approach?