But you can't escape the value that comes from those non-quantifiable elements like experience, market knowledge, strength of your team, state of the market to ultimately determine Deal or No Deal. 

@Andrew Semler Start by clearly defining and quantifying your goals and criteria.

That lowers their cost more and they can probably quantify the risk of you refi-ing in years 2-7. 2) The now 9-10K maximum cost is a drop in the bucket of their total theoretical revenue they stand to make over the term of the loan through the interest payments.

Before doing anything, I strongly recommend you clearly identify your objectives and quantify them.

@Jacob Albright The mother in law suite certainly does add value but the challenge is that it is very hard to quantify that value as there likely aren't many recently sold homes nearby of a similar size, bed/bath count, and condition that also have a mother in law suite.

@Bradley Fogeltanz Start by quantifying your goals and which is most important--cash flow or appreciation.

Instead, the gains on the sale of property are taxed only once to the shareholder, and can then be distributed by the S Corp tax free to the shareholders"Since we would be looking for him to sell us the property now and not in three and a half years, we are looking to help the seller by quantifying this additional tax burden so he can make a more informed decision.Does anyone have a good CPA who specializes in real estate that they would recommend to help me with quantifying this tax burden?

The most quantifiable, though, would be the comparable sales in the area (in SoCal, many houses will be very similar so you can find very accurate price point estimates for ARV).

How do you quantify a bad neighborhood?

But we as experts should quantify our future tenant/buyers almost like a mortgage lender....or no...?