I have a lot of questions, mainly about financials because I’m in a pretty unique situation. 

With the property address (and a Plat of Survey) I can give you more clarity as to your specific situation; however, at this point I have a feeling you are going to need to get a building permit in order to actually permit the work to be done to add the basement unit.If the Unit is already built out (recently or has been for years) the City will likely Still require you to obtain a building permit in order to "Legalize" the unit to where you could get the Zoning Cert to show 4 units...

Pick one that is commenting on your specific situation and DM them.

However, as long as value is 75k+, it should be a doable situation on a DSCR loan.

Or is it mostly just getting multiple biddings and deciding based on those options?

I would be interested to view these listings to determine if the locations, work needed, and potential cash flow made sense for my current situation. 

If you have access access to an 'Asset Protection Attorney" (Local), this is a good question to ask him/her.And also be sure to ask your tax person about the cost for maintaining either structure (accounting, tax, quarterly filings, etc...).Everyone always wants 'The Best", but (for instance) a Rolls Royce is considered one of the best, and it COSTS a lot more then a "Used Camrey".Getting expert advice on your personal situation is always best, vs just winging it based on someones response to an internet post.That being said, a Living Trust can own an LLC, but if that setup triggers an added tax return or two, IRS State and Local ($$$) is it the best choice.Which cuts down a tree better; a chainsaw, or a beaver?

Situations like that are exactly what I'm trying to avoid/address.

Mortgage rates are starting to come down so it will trigger a seller's market with multiple Bids/Offers so be prepared.

In my situation, if a tenant pushes back and threatened legal repercussions for a couple hundred dollars of damage, I simply give it back.