I've started to making two estimates, one for bare minimum, and one for going for more premium tenants.

For example, tenant behavior causes an insurance claim, and that claim leads to higher insurance premiums.

We have 25 units spread over 19 properties... which means we have 19 property tax payments, 19 loan payments (per month), 19 insurance premiums, etc. 

If not you will need to pay a premium to get a 3-4 plex even if work is needed there will be no value play.A little harsh I realize, but the scarcity of 3-4plex is real and you need to know what you're dealing with so if you find the right one you are ready to lock it up rather than screw around and lose it.

I’m not sure if slice or proper or cbiz would care as long as someone is paying the premium, but I’d be curious to find out. 

You want to talk to your CPA first and foremost you don't want to get in a situation were your deemed a dealer and lose your cap gain tax advantages.that said a take down schedule like this is common in the industry.. although CA usually a million dollar property is not a lot.. vis a vi development ground.. and builder developers there usually stroke a check if needed.I suspect though if your going to sell it in phases.the land would be split into 3 phases and you deed out each phase as he pays if off.. but not individual lots that were your CPA can advise you on dealer status.its common though in these scnerios to have accerlated paymentso you have  3 phases  333k each... you sell first phase for  400k.. second phase for 400k last phase for 200k.. this way you get a premium if he fails to buy the rest of the dirtalso in your contract make SURE you demand that all work product engineering soils geo tech that type of stuff is once paid for your property as well.usually in vanilla real estate transaction on the west coast I don't recommend or see the need for a lawyer but in this case I would find a good real estate lawyer tell him these basic terms and things you need then let him prepare the contract.. hope that helps.. and assuming the dirt is in CA.. of course.

Big insurance premium difference. 

If lender's experience is a rather integral part of the transaction and it's on-going operation it would make sense to have a premium over just a passive capital rate. 

Be careful working with some folks there because you will pay the out of state premium.

Keep in mind that insurance companies are great at cashing the checks for premiums but not that great when they have to pay.