Zoning, subcontractors, mother nature, P/I during construction and rent up, your loan doesn't get "fixed" until after construction, material inflation, etc, etc, etc.You have taken most of the risk off the table with family financing and family construction. 

The materials are outstanding and my understanding pre covid the networking and in person classes where very beneficial .

Tough time to sell a condo as inventory is crazy high and unfortunately, going to get higher as they keep building.

These situations are always tough but if you are improving the property, I think you have every right to increase the rent. 

My wife will materially participate in the business and I'll provide the financial backing.I've talked to a couple local CPAs and done a fair bit of internet searching on legal entity setup for my situation, but haven't been able to get a straight answer.

If you want "books, binders and educational materials" from real estate gurus and am willing to pay for them try ebay.

We've received a few quotes, but most are over $30k per unit.I've seen several posts on Facebook and Instagram BRRRR groups that do medium rehab for $8k-$14k per unit for both labor and material costs.

Great place to live and would certainly recommend, but the inventory here is tough as most investors are holding.

Commercial is very tough compared to residential to get into with limited funds/assets.

Same as you, I have never made a claim.Indeed it has been tough these past few years in the Midwest given the contraction of carriers and increase of premium.