Everything in your without permit benefits are either lazy, cheap, or cheating which doesn't usually go over well later.

It doesn’t make sense to me to just raise rents 2% per year if market rents are rising significantly faster.

Our local lender doesn't offer it. 

1) If you continue waiting for the "right time ”, you’ll always be waiting.2) Your current job doesn't care about you.

It generally doesn't make sense to build anything on the land to then tear it down and build something else, unless development explodes and you're tearing down ramshackle to build expensive.

When something doesn't sell, it's always price.

I'm being nit picky on purpose.Also, the Standard Lease doesn't apply to commercial tenants, so if the property under question is 6+ units, that might be easier.What you have described is Property Manager that has a Lease Option on the property. 

We take pictures on a pre-inspection only of existing damage, which generally doesn't exist because we repair anything that happens between tenants.

. $60k doesn't buy a whole lot these days that's not going to come with a pretty substantial amount of risk. 

Also the Voucher doesn't cover the security deposit which in most cases, I have to put my S8 tenants on a security deposit payment plan for those to get them qualified to move-in on my applications.