Ian,If you can buy a 3 unit that is at fair market value I would for sure consider offering the ask price.

The next thing would be connecting with a lender and seeing if you can find any properties that pass the self sufficiency test if looking at 3-4 unit buildings.

With my main goal being to house hack a 3-4 unit through owner occupancy then eventually moving out and renting my unit with naca it may take some years to pay off the mortgage.

Hi I want to purchase a 2 unit in Chicago but don't know I'd a conventional 97 loan will work if I put the house under an LLC at purchase. 

I inherited both tenants with their leases expiring at the end of May (bottom unit) and end of June (upper unit).

That way everything has a level of safety.

If you are looking for a generic 80-90% of purchase to fund with a good FICO score for a normal 1-4 unit, you don't need to spend too much time on finding lenders as you have plenty of options.

Your Realtor should be able to pull a list agents who participated in recently sold/listed units in and around the subject building. 

I personally wouldn't charge for any of that if they left the unit in good shape. 

In a better market you might be able to use those things to get a better deal on commercial insurance but in the current market there won't be flexibility.On personal policies/1-4 unit rental dwelling policies there won't be any flexibility whatsoever unless it's something the company already has built into their guidelines/pricing.