This resulted in a substantial $2500 reduction in the sale price.In summary: The place I bought from Ohio Cashflow was an old, broken down home that required frequent repairs despite having "significant" improvements at the time of purchase.

Providing more information about work completed probably helps most sellers because absent some sort of documentation on upgrades, or major work or accessibility to infrastructure, I'm going to assume that if it's an old building it has old plumbing and old electrical and submit an offer (or not) accordingly.

The house had a boarded up door & a broken window plus multiple stickers of pending foreclosure.

I talk to our local Section 8 office frequently as a property manager and in the begin they made it VERY CLEAR that the minimums are to protect the landlord AND the tenant.Most likely, the tenants are not going to have excess cash flow or savings to cover any of the damage to your "upgrades". 

I am not sure where to begin. with your septic and well you'll need to do site layout first with a land planner or the county. after that you'll need to check setback requirements and design plans and start budgeting with a builder. once you have a confirmed plan set and budget broken down and builder selected then you can talk to banks. most people think it starts with banks 

Too good of a deal to pass up even though Lennar is notorious for not giving way on finishes or upgrades. 

Your cleaning person should also let you know if you are short or need supplies (i.e. toilet paper, soap,etc) or if anything is broken or missing.I would create a checklist for the cleaning person of what they need  to clean every day, what needs cleaning once a week, and what needs cleaning once a month. 

If you're running a lot of analysis, it may be worth paying for rentometer or upgrading your BP account.

This property is about 50 years newer, and has all modern utility upgrades.

He is going to put the capital in to make the necessary upgrades in the place.