After sleuthing around the internet, it looks like it is recommended to hold  for a period for at least a one year before doing a 1031.

Millions of people and many 10,000s of programmers have tried to monetize the space.

Other than cleaning fees, you should make sure you factor in higher insurance rates that cover STRs, utilities, internet, consumables (toilet paper, soap, etc), landscaping, snow removal, linen replacement.

@Lauren QuestProperty analysis is a specialized skill and you can learn by practicing it.There are various calculators available on internet, depending on type of property you want to analyze.Its very important to understand the strategy and investment goals.Good Luck!

There's lots of stuff on the internet that can probably explain it better than I, just do some more reading.

How can I find people's information for free?

I like the property for this use or personal, so I'm not sure how I want to proceed.Property Type: 2 bedroom, block to the beach, condo w/ association fees (they allow STRs)Sale Price: 275,000Loan: 10% down conventional, 3.5% over 30 yearsCash Invest: $61,250 (assuming $27,500 down, plus closing costs, plus 20-30k rehab to spruce up for us or short term rental)Expeted Income: $3500 per month (obviously summer is busiest, AirDNA thinks 48k annually (4000 per month is expected), trying to be conservativePITI: $1,735 per monthAll Expenses (CAPEX, maintenance, stocked goods, heating, electric, internet, water/sewer, HOA, city fees): $1,265 per monthCash Flow: ~$500 per monthCOCR: 9.8%Obviously my primary concern is making sure I'm not outrageous on my rental figures, and want to know if I've accurarely covered typical expenses on a shore AirBNB property.

I don't know what you think is condescending, but I've been investing for more than 30 years and can tell you that what you are doing is going to leave you in analysis paralysis for another year and then you will rely fully on someone you met on the internet for your first deal and you will lose that money from soft oversight and not taking advice and interpreting anything other than a pat on the back as against your goal.

I just download whatever is free on the internet for a lease but it's a headache getting it into Docusign so I would follow the advice of the guy above who uses TurboTenant. 

For the people who get discouraged and feels like wholesaling is “a lot” the only main thing is knowing how to talk to people.. everything else will work out for itself and don’t believe everything you are taught about wholesaling even from people of the internet; meet with someone who wholesales in your city if you find someone willing to do it its a price you can never pay back to them.. all I’m saying.., don’t stop when they it’s “hard” they could really just be trying to stop the next best you.