After attending an awesome BP meetup in Philadelphia (hosted by @Troy S.) some red flags have come up regarding the structure we're looking to use to fund our first flip.My partner, @Phil Sabella, and I have connected with a financier/partner who does JV's.  

As for myself, I have been an agent for 8 years and have been dealing with tenants and tenant screening ever since I started so for me it's something I'm good at, have systems in place to minimize the time it takes from my day, and is something I couldn't imagine paying someone else to do for me at this stage of my investing "career".

I agree with the answers above and that condos have a lot of red flags for STR investments.

Pricing just made sense for me at the time.

The company red tagged it.

That right there is enough of a red flag for me.

I actually ended up deciding that quickbooks wasn't even worth it for me at this point.

I remember the reports of the first cases coming out from Wuhan in December of 2019 ,and obviously since everyone knows there are only 4 comprehensive bio safety level four laboratories on the planet, Moscow, Paris, Fort Detrick-Maryland and of course Wuhan Institute of Virology, and given that there are over 100,000 small town with wet meat markets throughout China, one doesn't even have to ask the question "what are the odds?"

In short, if you're not renting every week of July-August and every weekend of the winter, you're taking losses, particularly given the ridiculous prices I'm seeing new investors pay farther north in vacation areas like North Conway or the White Mountains.And looking solely at North Conway's recent court case is a red herring: plenty of small towns around the NH continue to enact knee-jerk reactions and excessive permitting/regulations as a reaction to STRs assumed role raising housing prices and shrinking supply for local residents.

I'm sure there's money to be made there in real estate, but it seems to be heavily reliant on one industry (Army) which is a red flag for me when it comes to evaluating markets.