A few things to keep in mind:Section 8 requires the property to pass an inspection based on HUD’s Housing Quality Standards (basically making sure it’s safe and well-maintained).The rent you charge has to align with Fair Market Rents (FMRs) in your area, so it’s good to check what similar properties are renting for.You’ll still be responsible for maintaining the property, but the upside is that a chunk of the rent is guaranteed by the government, which can provide steady income.Check with the local housing authority about any specifics for your area—every jurisdiction does things a little differently.This could be a great niche if you can find a good deal on the land and make sure your expenses (like maintenance, insurance, and occasional vacancies) are covered by the rental income.

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).

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

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

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.

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

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.

Can you please send me over any recommendations for insurance agents in Ohio.

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.