And what is the likelihood that they would be able to reimburse you for those storage fees, really.If there was damage to the property prior to the imprisonment and the security deposit won't cover the full amount of damage, can you sell their property to recoup expenses for damage?

I haven't had to do it, but would use their security deposit to buy the insurance, then reimburse the deposit when they paid me.Send them a letter specifying the lease violations and cite the specific terms in the lease being violated (paragraph 10 on page 2).

But it is a 4 unit building with 4 owners, and we have always just operate by having the owners fix their issues then seek reimbursement from the HOA account so as to not having to go through too many steps to solve simple issues.

In MA you aren't allowed to charge the applicant, I did that a couple times without knowing and ended up having to send out multiple checks to reimburse the ones I denied. 

If the tenant can get reimbursed by the prior landlord, your response is "So what and who cares."

Could we then have our agreement be that he keeps the agreed upon $100,000 ($85,000 owed on the mortgage + $15,000 profit) and pays us the difference, thus reimbursing our construction costs and giving us profit?

You can indicate in your listing agents are reimbursed through the tenant.

I'm just worried I'll end up submitting a bunch of deals (if they don't accept the initial one I have planned) and never secure one they deem "appropriate" (and therefore forfeit the entire $3000 since I will never GET an actual loan to pay back so I can get reimbursed at the end of the term).

I prefer my tenants drop off the application in a drop box.On a side note, I have heard of some people on here in tougher areas, make the application fee reimbursable towards the first months rent. 

And chances are, our property policy will close out and seek reimbursement from the Gas company.Bottom line, if my client would have to wait for 1, 2 or 3 years to have the gas company pay for the damages and lost rents, he would loss the property because he can not float that much $ for that long.That's the one I have this month:)