I had already factored in self management...I’m just wondering how people do just continuing STR over the winter months.

When the city comes after people, they go to the owner.

There are quite a few investors who attend that meeting and usually a few contractors.If you need any other referrals for your team let me know. the people on our team are great at what they do.

I chuckle everytime I see people in real estate want to remain "anonymous" as it is nearly impossible unless you have a boat ton of money to spend on remaining anonymous. 

During the refi boom I had people cancel on their lender and switch with me after they had signed closing documents(this was during the 3 day right of rescission for the VA loan) you may incur costs such as the appraisal, but other than that you shouldn’t owe anything to the lender.

MANY people have wishful thinking and do not correct whatever is keeping them from getting a mortgage. 

I always send people in the direction of @Amanda Han she is among the best in the nation when it comes to serving real estate investors. 

So with that, I'm looking at putting out about $3,966 and bringing in $3,166, and that's if I self-manage.

Be wary taking advice on these forums from people who are not experienced in the niche you're trying to break into.

Steve, the question should be more along the lines of whether you want to build a retirement fund vs try to bring in passive income now.