I cold emailed and called the owner multiple times and eventually we connected, met in person and made a deal over the course of a few months.How did you finance this deal?

Sorry to sound cold.

Air conditioned air leaking to crawlspace making crawlspace heat or cold depending on season causing more power bill to tenants.

Bloomington has milder winters then we do up here in Chicago, but still gets snow and cold, which takes a toll on the property.  

So here is what I do:1 - Get buyer criteria for what they are looking for (exact criteria)2 - Go source that criteria using data provider3 - Scrub the list and plan a marketing campaign around it (i.e) > Direct Mail > Cold Call > SMS > Online Ads > Social Media, etc4 - Once I get inbound leads coming in.

I totally get it—starting in STR can be tough, especially when cold calling and emailing aren’t working.

We are attempting to get an eviction date, but could not pass a lead paint inspection because the weather is so cold in Cleveland that the paint will not dry.

You're increasing the need for hot and cold air dramatically and it's doubtful the existing system will be adequate.But, in answer to your original question - yes you will need a permit.

@Chris Seveney although I suppose anyone looking to do a syndication cold do it from the PMC to find investors. 

Rents that are significantly lagging market go up $75.I chose the Winter timeframe because no one wants to pack and move during the holidays and cold.