You don't have a hold or sell problem, you have a budget and or income problem.I'd review my budget and prioritize saving the goose over lifestyle comforts. 

Always stay mentally prepared for something to come out of left field.

Ideally, I hope never to have to tap into this account.During the early stages of adulthood, I prioritized paying off loans before allocating money to my Investment Account.

To have any business, you have to have a degree of toughness, mentally and physically. 

As a Contractor myself, my biggest challenge is staying in budget as much as i can, making sure the investor is not building a house for himself to live in as it happens in a lot of cases and they lose in the back end, and staying on schedule.Budget: I can give a ball park number and where we should be at Sqft costs, as long as the investor doesn’t go Crazy, I usually am within +$5 of my proposed Sqft CostsInvestor: Rookies have the same mentality, Let’s build this flip like we see on TV!

She could be a complete a-hole or mentally ill or someone that prefers a full head of hair.

So you want to make sure you are mentally prepared for the hard work going in and are committed to see it through.

Maybe it was just the ski/vacation mentality but guests destroyed EVERYTHING and it wasn't as easy to chargeback as you seem to say it is now.  

Some people prioritize cash flow while others will prioritize quality of life. 

They need to schedule, or change an existing schedule with other customers to prioritize yours, or perhaps even lose a job to address your priority task for additional cost.Was a detailed "scope of work" prepared and provided to you by the PM so you could get an equal and fair estimate from your source?