As to your point about first year hurdles; yes it is important to keep in mind that property ownership is really a long-term game.

Many commercial properties (5+ units) have a $250-$400k minimum, so that may be a hurdle. 

I didn’t anticipate this to be a hurdle since I thought hard loans were turned into cash pretty readily. 

That said it is thier kid and they can parent how they want.not an unreasonable request.

I know that renting up your investment can be one of the most confusing and nerve-wracking parts of the process (especially in a place with as much bureaucracy and legal hurdles as Chicago) and am more than happy to talk with anyone about that.

I can’t imagine what hurdles you would have to go through with the HOA to add a bath and/or bedroom. 

Additionally, for rate-term refinances, many DSCR lenders have no seasoning requirements at all.Easier qualification: DSCR lenders have much lighter qualification requirements than conventional or portfolio lenders, such as no DTI, income verification, or tax return hurdles that can slow down or disqualify loansFlexibility: While conventional and bank lenders are heavily regulated and follow standardized rules, DSCR lenders have much more flexibility and control over their guidelines.

Maybe it's priced aggressively enough that they think someone will buy it based on the limited info available on it, or maybe it's a FSBO deal and the seller is unreasonable, or maybe the listing agent is doing the best they can dealing with a difficult or hard to reach seller, or the seller has sloppy accounting, or they died, or the listing agent is incompetent/inexperienced, who knows?

I've heard one of the most difficult hurdles is finding a contractor that qualifies through the program and is willing to jump through the hoops. 

Seasoning will be the hurdle for some lenders on this one.