I think the big question is how badly do you want to keep the extra $50k liquid?

At 6% I’ve only saved $360k, but you would have saved $720k, an extra $72k/yr.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

You are not paying for their services and won't cost you anything extra anyways. 

If you are a Dr. who is investing for extra returns and do not have a worry about Capex then invest the $300.

The inspections have become so nitpicky over purely cosmetic items there has to be an extra $1-2k per year to keep up with the punch list every 1-2 years.

I have studied things and I feel I would only make maybe an extra grand a year and frankly I don't want to squeeze every last time out of people coming for vacation.Most of our guests are regular people.

For me at least, doubling my profit is well worth the extra two months of expenses on the market.

Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment. 

An in-house attorney would focus on resolving issues efficiently rather than driving up fees with extra billable hours, which can happen with outside firms.That said, I’m questioning whether this is the best perspective.