Contingencies will not impact insurance companies policies.

If I have a 14 day inspection period contingency in my contract with my seller, Do I give my buyer a new 14 days to inspect once he signs the assignment contract?

Once contact is made all you should be focused on is getting that sale agreement signed with a 30 day closing contingent on inspection.

However, we are currently under contract on the 20+ acre property, contingent on my Dad obtaining a refinance on his home.

He is worried you will fail the finance test... if you are comfortable, give him a big EMD and waive the finance contingency. 

I started out with sweat equity, moved to the point where it was a contingency plan if something went wrong, and now I am rarely involved the physical side of remodel projects.

Sounds like you want him out now and money motivates a lot of people.Make it contingent on the condo being in good condition and professionally cleaned so that the expectation is set before handing him over any money.

You'll also want to look over the financials to see how well the property is being managed and to make sure there is a healthy contingency fund in place.

And hopefully one that will do it on a contingency basis.

Basically - do you have to have the property in hand first, or will hard money lenders make the loan contingent upon the property going under contract?