I have no doubt I could work twice as hard and find a better price on this or that but also know that the pains and potential problems that would come with vetting and working with a collection of new vendors that may or may not be reliable or do good work are not worth it to me. 

- Is it a painful process?

@Chris Hillthis decision is painful to say the least.

When it comes to painting exterior, you're looking for someone to pressure wash, prep the exterior (taping), caulk and seal where necessary in small cracks, around windows etc, prime and then pain with 2-3 coats.

We started off renting to students and it was open for the summer for us.It was a pain moving stuff out when school started back and we didn't want to fix it up for students.Some how or another I decided to try the vacation rental and it was an instant success.

Septic issues are always big pains in the buttocks.   

I heard it was a huge painful process.Property Management can do this.Also, your idea is fantastic lol.

.), I'd cover the new appraisal fee, since I share responsibility for this due to having been the one to pick the lender.If you're working with a direct lender, then it's more  of a pain in the butt, and you will likely be on the hook for the new appraisal fee.

Nice thing is that many banks offer low/no closing costs HELOCs with no upfront application fees so you shouldnt feel too much pain if you have to apply with a few banks.  

That man has sacrificed more than I can imagine in my upbringing and as a result has zero retirement funds. 40+ years of night work has taken a toll on his body and it pains me to know he can't afford to retire.