This issue is not a one off occurrence, it is very common place.

The issue is that if you lie and the policy doesn't coverage for renters you might be essentially uninsured.  

If W-2 income is an issue for you, maybe try to 1031 into something 5+ units that way you can use commercial financing which wont factor in personal income as much 

Examples are mobile home parks, RV parks, and golf courses where the value of the property is not primarily derived from building(s) but rather from the improvements to the land.

I signed up for an apartments.com account so I'll offer them that option right now and if they have any issue, I'll work on a payment system with the bank.

This way I can track P&L by state and satisfy any state tax issues, know how much I make on each property, and finally how much for each tenant.

Issuing a W2 to my daughter will not help.A 1099 or a sublease strategies will trigger self employment tax on her, but her income is way below the standard deduction, it should not be too much. 

Hello Jesús,I have alot of experience with dealing with this issue.

When we first bought used 20 foot were around $1,800 to $1,900; moved up to $2,200 then Covid and supply chain issues hit. 

You're right, I'm just being cheap, I'll go out there, it'll save me stress and issues in the future if I can go this one time, plus I want to meet my handyman and future cleaner in person and go to a meetup as well if I can!