Primarily, the government wants to validate that you spent what you said you spent, and substantiate that the charges you made were actually for business purposes (especially when being used to reduce your taxable income).

I've always worked under the following givens:-I try to leverage as much/best as possible, therefore have a decent amount of debt-I try to lower my taxable income by writing off as much of my expenses as possible, therefore my year end statements often show minimal gains, sometimes even losses even through write offs, even though I am making money.

I think you're getting much closer to market value than you were when up over 220k, but you may need to decrease more if determined to sell this year. 

Then I ask, "Would you say that our lifestyle with regards to more time with family and more leisure time and having less money stress has increased or decreased?"  

My question is can I take out any of the funds from the proceeds as non-taxable if they are less than the purchase price? 

You should prolly suggest the individual with the IRA to consult his/her own team.The reason is that if anything is done incorrectly on the individual's end; the distribution can be considered a taxable event and the individual can blame you for the incorrect advice.I agree with @Eamonn McElroy that you can potentially create a partnership and have the acres of land used as collateral for the loan.

When you make a claim, the insurance company does not want to pay, and will challenge large claims to avoid paying or decreasing the amount they have to pay.

Sorry for the long post. 1) 10k on your side: if this was improvements, you can add this to the basis of your property that will decrease your gain when you sell. 

When you decrease the amount of loan types available then you reduce the size of your buying pool so your potential sales price is decreased. 

If you buy a property at 100% financing and don't add equity through raising rents, decreasing expenses or renovating the property, you will have a tough time getting out of the Hard money loan.