I'm assuming they'll need to have their own renters insurance because my homeowners insurance won't cover their belongings.3) I don't close on the property until the end of June.

It is, admittedly, a more complex strategy with the attendant risk of having that mortgage payment to cover whether the property is rented or not. 

But if you're buying a condo and the rent doesn't cover mortgage and fees, you're HOPING that when you sell that you can sell the condo for greater than the orginal price you paid + mortgage interest + condo fees.... 

That included cutting the concrete, installing window/outside frame/cover, and hauling away concrete.

Approval letter should refer to the accepted offer and state you have sufficient funds to cover.

You need to make sure that your first rental the rent covers: mortgage, insurance, percentage of repairs, percentage of vacancy, percentage of property manager (optional), taxes etc.   

After being burned by tenants that get behind and never end up paying and lead to eviction I now state in my lease that we start the eviction process the day after the rent is due, but I make sure that is clear form the beginning and if they fail to pay then we charge a late fee and start the process of eviction based on my states requirements.The reality of the matter is that if they don't take the rent out of their paycheck then they most likely wont pay the rent, if they do then they are borrowing money which will put even more financial burden on them and make it less likely to pay on time the next month, or they are waiting until their next check to cover the rent and then will have a hard time catching up in order to pay on time snowballing into perpetual late payments.If you really think about it allowing a tenant to get behind on the rent ends up hurting the tenant, you are not helping in any way.

I am trying to figure out if the TAKL app has actually reasonable penetration in coverred markets.

Granted this often covers roof repairs, exterior insurance, lawn care, sewer and some other expenses.

Example:  I always want to be able to cover one month of rental income ($3,450) for my annual Vacancy reserves.