We sold the Bucktown property in late 2020 in order to buy a single family in Glenview in early 2021, and now the Lincoln Square property is a full-rental bringing in $7,200/month.

Good Afternoon BP forum!  

My wife and I, along with a third partner, are looking for a short term rental (AirBnb, VRBO) out of state to purchase late 2021/early 2022.

Homes in range of $75K a couple of months ago are hitting the market at $95K range lately.

TLDR: Agent had only two showings in 6 weeks, was too drunk (puking) and listed our property 4 days late, my business partner and I had to constantly follow up with agent, constantly told us we were priced correctly so we rejected a lower than asking offer, now saying we should have taken that offer.

It’s not too late to get started.

The court case you are referring to happened in late 2017 and the precedent is that if you collect things like last month's rent it needs to be help the same as security deposit and is considered security deposit. 

If the appraisal comes back at the agreed price, it is too late to ask for a price reduction. 

@Michael IcbanIn Canada an investment property requires 20% or more down. 25% is becoming more common lately.

If the roof has already been redone, it's too late to put that down.