Also note that my company will possibly either cover closing costs if we sell or provide property management for two years if we rent.

They will take the permit fee and send an inspector that will provide some assurance that the work was performed correctly.

•For example, a listing with three price drops and 180 days on the market would be weighted less than one with 30 contacts, no price drops, and a quick removal after 30 days.3.Open Data:•Provide direct access to each comp’s details: price history, leasing schedules, photos, and even links to the original listing sites—all without leaving the platform.These three issues have been my biggest frustrations with current tools, and I’m building this out for internal use in my market.My questions to you:•Is this something you would want to see in your market?

Also, providing value to others at a high level will pay off for you in the end if you stick with it.

Would the info you provided still be the same?

I may have to Teak my strategy in light of the excellent advice you provide here, Henry.  

All that to say, I'm not sure when they will want to cash in and sell the lot due to the appreciation the subdivision has provided.

Just stating that waiting will also likely make the cost of what you want to buy go up if the last 98 years of real estate data provides the future direction.

Some general pros v cons - I'm sure other people will provide other insights as wellPros: -Above market rents- Monthly rent payment on time that you don't have to worry about or chase anyone down for (if full pay)- No shortage of tenants depending on your standards - Tenants are incentivized to not trash/destroy the unit, otherwise they'll lose their voucher (Yearly inspections made by local S8 inspectors to keep everyone honest- Rental payouts are normally adjusted 1-2 times a year to keep up with market rentsCons:- May take a little while to get onboarded - dealing with local govt can always take longer than expected   - Generally won't have a super high credit score (to be expected given it's the govt paying for rent)- Each unit will need to be inspected and meet a certain living standard in order to be approved for fundingYou'll want to make sure you work with a property manager who has extensive experience in working with S8. 

Definitely reach out to your insurance provider.