I am thinking in terms of maximizing my taxable writeoffs. 

Unfortunately they couldn't be reimbursed with 1031 funds without those funds being taxable.  

Both refinancing and HELOC are not a taxable event, they are loans."

Currently appraised at $1.75M in the Boston market and the $500K of gain under section 121 and the $35k purchase price would still leave a taxable gain of roughly $1.2M.So essentially, doing a cost seg doesn't make sense?

For example, weekly tips like paying your child up to X dollars per year for job site work (ie: post construction cleaning) before they will get taxed on that income, which ultimately helps you, the business owner, by reducing your taxable earnings.Thanks! 

@Mark Statner - You want to use the tax assessors website for determining a houses square footage and taxable assessment.

You can purchase less than what you sell but you will pay tax on the difference just as if you pulled profit out of the deal.I know, you put the money in the first time and it's not taxable. 

You'll get the deed and assume all liability, your father gets a smaller taxable amount up front and payments over time.

To self-certify, a taxpayer merely completes a form (which will be released in the summer of 2018) and attaches that form to the taxpayer’s federal income tax return for the taxable year.

However, profit from flips cannot be exchanged (legally) so you'll have taxable proceeds at the end (assuming all goes well :) ).