Vrbo filled my calendar.

I am aware most leases coincide with the academic calendar, however, I am hoping to have it rented by April/May.

Do they have interesting classes on the calendar?

I go to furnished finder and I see couple of of listings, but quality of pictures are bad, and I have no idea how full their calendars are. 

but it sounds like you know a lot of what you DON'T want; what you do want is the opposite. if you're going to do your next project alone, it sounds like you want a LTR nearby that's relatively turnkey without any problem-tenants. you can do a 'lazy 1031' where you just sell traditionally & in the same calendar year buy the new property, while working with your cpa to figure out how to offset the tax bill. you could alternatively partner with an active investor on your next deal; that way you could invest in what could be a higher cashflow market compared to where you live, and not have to invest much time (since it sounds like you guys don't have as much time to spend on this now). 

If you want to make 1031 work and mitigate those taxes you can modify your flipping calendar a little bit. 

1st Question: Check out real AirBnB listings in the area, and dig into their calendars / cleaning fees and rates / AirDNA is a good tool for determining seasonal variance, but not much else.

@Andrew B.2020 tax year income tax returns are due more than 12 months from now (assuming a calendar and not a fiscal year). 

Deals aren't a good substitute for time in the business, because a lot of things happen with the turning of calendar pages.Just my perspective.

Once leads are pre-qualified, they can then make an appointment based on my schedule through some online calendar.