You will have to understand if you are finished with the heavy lifting on the maintenance.

Do the properties you are analyzing need no renovation, light, or heavy?  

He is my contractor and I have worked with him for 20 years or so but he also comes in and acts as my “heavy” when I have a tenant issue I need help with as he’s been doing property management for other people for years and years.

Achieving 2-2.5x base rent in rental arbitrage is highly market-dependent and may work in tourist-heavy areas but is less realistic in stable markets like Houston.

Her undergrad is in design with a heavy dose of building codes, etc.

The two suggestions I would have are:- Amount of text in the Year to Date section seems heavy.

Try these options before busting out the heavy duty chemicals.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

Our market is very heavy tourists, so a lot of individually owned STR condos, but honestly I've personally have had more success in long-term rentals doing the BRRRR strategy with small multi-families and B-Class SFR's. 

Unless there is a heavy value add aspect, seller financing, assumable loan, or some other "deal".