It is a 2 unit property and we are not planning on adding management.

No new square footage is added in converting the common living spaces to bedrooms.

I'd only play with extra money and pull back gains as it's super volatile.And it's not investing to me.

LeadSherpa is a good service i had a lot of experience with if you want to go that route.The two best strategies I’ve found are inbound methods: direct mail and Google Ads.Direct mail can be expensive, but it can also yield highly discounted properties.Google Ads, on the other hand, doesn’t require data extraction like calls, direct mail, or texting.

If they take an extra four days to vacate, that's $800 in holdover charges.

We've owned this property for 15 years and only once had an issue with a tenant who claimed they weren't informed that it was oil and threatened to sue due to the added expense.

So you as an owner, would you be willing to ask for less to have your property rented quicker and "lose" the extra $1200 or so per year or would you rather lose that $1200 per month because your property is sitting vacant.In regards to demand, Cleveland is one of the top Sec8 markets out there. 

Removing a wall could add value to the home in theory, but for some rental areas, having extra rooms helps.

If the answer to both added questions would be "yes", then you have a potential goldmine here.Combining the seller's concerns, and the reality of a big down payment being a negative to the seller (see Q: 1), you should be able to set the terms, with a lower DP, and controlled interest rate, to have this property CF and,...be able to sell the package to another REI down the road,...as long as you buy this using an LLC (a new one). 

Sometimes it's better to only put the minimum down because the break isn't significant enough when you put down the extra 5%.