Take a look at the rents for both sides vs current mortgage payment (if any), new payment on the cash out or HELOC, taxes, insurance and HOA (if applicable).

Before listing it, I had lots of expenses, including painting, floor refinishing, plumbing repairs, staging, cleaning, etc.In a 1031 exchange, I purchased two small multifamily homes which also have some roof work, painting, plumbing, etc. 

I waive escrow on all my mortgages and pay taxes/insurance with cc, put repairs on cc, etc.

You think through the major systems in the house (roof, exterior or tuck pointing, hvac, plumbing, electrical, unit turns, common areas) and if they are all new you should be good for a few years (5-10). 

There is no insurance that covers an increase in HOA assessments. 

This seems like a lot of work to save 15% of $35k in taxes (Less than $5k.) especially if you have transfer taxes or title insurance, or you convert your long term 15% rate in to your son’s regular income tax bracket.I hate paying taxes as much as the next guy but this lemon isn’t worth squeezing.

The problem is that you have to accept the dog but the insurance carriers do not cover bites from Pitbull's.

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

Yeah, insurance is likely more than sufficient for most investors.

Prepaid items are comprised of property taxes and insurance and prepaid interest.Property taxes and homeowners’ insurance will depend on whether or not you have an escrow account, when you are closing, and when those items are due.