Assessing brokers based on their transaction history and success in the market carries more weight than simply focusing on the highest price offered.

If you can’t quantify risk and don’t understand the mechanics of “weighted” average of expected return and range of returns (standard deviation) then you are at a severe disadvantage and should consider a competent investment / financial manager for your investment capital.  

Contrary to what everyone seems to be saying these days, a good agent is worth their weight in gold.

Some strategies to lessen the negative cash flow are: house hack and rent out the other unit as a mid-term rental (to traveling professionals or for people temporarily displaced because of insurance reasons like fire) or short-term rental (business or vacation).

Like, for example, if somebody came on here and said that the doctor told him working out and losing weight saved his life and he was extoling the virtues of exercise and your response was that it's "just working out, it's not really a big deal" - YOU'RE BOTH RIGHT. 

Have you paid their standard fee (or beat them up to lessen it further) or a premium to cut the line when updates or revisions are needed?

There is a lot of weight on marketing, and a lot of inputs to that cycle.

If it is block construction the engineers will make you beef up the slab and add piles to support the new weight of the second floor.

After weighting all of that, does it make the most sense to try to keep this tenant in place? 

I find with ANY project on a property, PLANS are worth their weight in gold bc they will show the exact inches, ft, etc that the project entails.