Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

Looks like you guys have a lot of port silt loam, which is NOT a very expansive soil.

Loan seasoning requirements are usually based on the note date and the loan purpose, like cashout refi. 

My cousin works for a hard money lender in Milwaukee and they fund projects like this. 

Likely will reduce to whatever market rent is on 1007 report, if the Section 8 income is higher than market.

Shelf LLCs are pre-established entities like you mentioned in your post.However, if you prefer to avoid setting up shelf LLCs, using land trusts can be a simple and effective alternative.

It sounds like you are overly confident in your Excel spreadsheets..... 

The latter might not let you do anything and is more likely if they don't like your tenants.I see 3 scenarios:The fence is on your property.

Agents don't always know what they're doing or they throw things against the wall and see what sticks.Even if you could purchase that, you'd likely face massive coinsurance penalties in the event of a claim since the property would only be insured to 57% of the actual replacement cost.If you've already shopped the policy across multiple companies and brokers, it's likely that the prices you're seeing are the prices you can get. 

If it is a contractor that is more organized they will likely do this already, if they are shooting from the hip "based on experience" they will likely just give you a total $ value.