I purchased a single family home good quality location in Chicago’s Northwest Suburbs in Cook County as a personal residence. At the time of purchase, I knew I might not want to stay indefinitely and at some point to...

A no contingency sale would be more common in a severely distressed non-functional property where there will be so many material defects that the buyer could not feasibly negotiate until they evaluate them.  

Is just the fact that no garage could be a no go for some buyers enough to build it even if it only raises the value by the actual cost?

If the market rents do not cover the mortgage, you may do a no ratio DSCR for a higher rate/reduced LTV  Which most likely the 1007 will be nowhere near the revenue generated by a PadSplit operation.

We sold a wonderful two unit STR in Depoe Bay in 2024, which generally is a no-go zone but has neighborhoods with specific commercial zoning that allows for vacation rental usages as well as a brand new development of luxury homes that allows STR usages similar to Olivia Beach in nearby Lincoln City. 

Just know that it is a "no days off" kind of business and very mechanical.I would suggest documenting your process via video so that eventually you can bring people on to replace the different hats you will be wearing.Keep in mind of these 5 components of any wholesale business.lead generation, deal sourcing, underwriting, marketing, transaction coordination.

Two things I remember that probably don't happen today: -First property was a no-doc loan, technically low doc because you still had to provide information but with 30%+ down pretty much anything you wanted was yours.

Quote from @Andy Sabisch: Question . . .our leases have a NO SMOKING INSIDE clause. 

If the answer is yes, then it's a no brainer to make minimum payments on your 2.8% interest rate mortgage, and use the funds that you would have paid extra to pay it down faster, to either invest in more real estate, the market, or anywhere else where you can get a ROI > 2.8%.If the answer is no, then feel free to aggressively pay it down as fast as possible, to become debt-free faster, and just have a large amount of money in savings or to splurge with.The bottom line is that your 2.8% mortgage is GOOD debt.

If the renter has no way to take care of the pets and you do not want to keep them due to their cuteness and friendliness, then an option might have to be a no kill shelter.https://www.nokillnetwork.org/