I often have tenants who don't pay the last month's rent because they think the security deposit will cover what is owed. 

I will be paying about $44K out of pocket back into my HELOC.

I hope you don’t have friction with your partner because the money got ahead of the work.I’ve had some success hiring workers for the day at the prices the gcs pay them $100-200 but have had my fair share of misses here too.

If that person were to get hurt somehow and then expect you to pay the medical bills or become disgruntled in some way it is just a phone call to DOR, OSHA or L&I. 

I can't really afford to pay two mortgages.

Despite paying fees, doing a deal and making some profit is better than sitting on the sidelines. 

Refinance and pay the downpayment.

Very commonly the resident pays a portion of the rent so your rent increase will affect their budget and their lives. 

A HELOC offers flexibility, as you only pay interest on what you use, but rates tend to be variable.

I own all my toys, never seriously worry about money (I suspect everyone with any money always at least pays attention to it), spend my winters in Florida and rarely work in any sense (I do some consulting and side teaching) more than 10 hours a week.