For example, Woodstock has policies that mandates that short-term rental owners rent to guests no more than 180 days per year and no more than 26 weekends per year.

This isn't totally necessary, but meeting property owners if you need to is a great way to win a deal

Nate @Nate Marroquin   You can use the income from your tax returns on the current rental adding back your paper loss (depreciation) and add back the mortgage interest, property taxes, home owners insurance deductions on your tax returns. 

Most work like this: Rates: 9% to 13% (Most Deals are 11-12%)Terms: up to 36 Months (Most Deals are 6-12 months)Fees: 2-4 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 (For loans less than $250,000 $2,500 minimum fee)Max Loan: 65%-70% of After Repair Value(ARV)100% Rehab Financing Available (Require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 2 Weeks)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

We used those extensively when we wrapped owner contracts ?  

Maintenance at at PM company or one of the big hedge owners like AH4R, leasing at apartment complex will teach you a lot about applications, fraud, leases, collections, evictions. 

I have already sold by owner and am well aware of 1031.

You do the course and you decide you want your money back. 

Best wishes with whatever you decide.