Either way, I will be very specific and intentional with vetting the property and numbers before I go through with the sale.

I think guests hardly ever damage things intentionally, but when you have luggage coming in and out all the time and little kids running around a "new place," there IS a lot more wear-and-tear, scuffs/dents/scrapes, and broken glass. 

If your intent is to scale, I agree with many of the others that have mentioned how cumbersome that would be dealing with so many different cards and properties.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

Two weeks later I stopped by the unit (was passing by and decided to take a look) and found that someone was using the shower and leaving food and clothes in the house with visible intent to return.

Have you ever been totally open and honest with a seller or agent and tell them you have no intention of buying the property and don't know the true buyer when you offer and won't tell them the price the true buyer will pay?

W2 employee in 2 full time jobs with the intent of investing in real estate to get some tax relief and generate cash flow. 

A big thing the IRS looks at is intent, and renting it out for at least a year shows that you intended to use that property for investment.

It is your property so unless the tenant is intentionally breaking things they should not have to pay for repairs.As others have mentioned, it is hard enough to get tenants to report small issues that can and do cause larger problems when I am not charging a fee, you are opening yourself up to major issues if tenants are reluctant to call because they don’t want to pay a fee.

As for speculation that this building would be leased by BiggerPockets - no that is not my intent, and I would feel it is a conflict of interest.