Rents on the 2 units in the residential units would be increased in the next year, as they are at least $100 below market.My dilemma is that improvement of a roof does not add major value, and given this is considerable cost, I am not sure if it’s still a good deal.

Up to you how you’d like to proceed.Let me know what would be the best way to access the inventory you recommend and we can go from there. 

He is experienced and frequently has access to off market deals.

Courtney Huntoon in my experience (Class A SFR and multis) incentives make everyone feel good, but don’t actually produce any improvements in NOI.

You can use the search feature (magnifying glass in upper right corner) to access the more popular ones. 

Obviously this is all dependant on ARV and budgets, etc.Again, this is all just spitballing thoughts but it still intrigues me from a standpoint that you are working together as a family group improving everyone's position.  

Would this be considered BRRRR or should I try & refinance this property after I make some improvements.

Most folks don't have access to cash to replace mortgage. 

If you have access to USAA, they have good rates and you can have up to 10 rental home policies with them.

Furthermore I see a tenant who lets me know when there are issues as an opportunity to keep looking in on the place AND with more improvements that I make to the unit the greater the appreciation in value....