It truly is a close knit community with tons of experience and knowledge to share.

The Chicago Neighborhood Initiative has rehabbed a decent amount of homes on Champlain and Langley, and 30 more distressed assets will be coming alive shortly, so there is progress - https://www.chicago.gov/city/en/depts/doh/provdrs/housing_resources/news/2020/july/city-grant-approved-to-restore-30-historic-pulman-rowhouses.htmlYou are right, inventory is extremely rare down there as it's tight-knit, not a lot of trading, and when it does, owners tend to trade with each other.

It's fairly close-in, has a tight-knit, diverse community with a strong neighborhood association, minutes from i84 and i205 as well as the Max lines to downtown Portland and Clackamas and median home values are low low $300s but there are still plenty of houses to be found <$300k. 

I have had inspectors knit pick on certain things outside that needed repaired.

Not to mention, you have access to a close knit brotherhood of guys you spend more time with then family to involve in your new syndication opportunities. 

MH park neighbors are usually tight-knit. 

Considering they are military, you are likely in a military town, and military folks are part of a supposedly tight knit group, being flexible with them can lead you to your next tenants through their reference.

If you are looking to raise a small amount from a close-knit group, as @Jacob Blackett said, you could probably do a direct LLC. 

I don't want to be the knit picky type of LL that tries to nickle & dime people but I am trying to find that balance that is general wear and tear and what is excessive wear and tear and should be taken out of the tenants deposit.

I have a pretty big doubt it's "City rules" and more of "Our tight knit clicky group who are on a power trip and want to cry if everyone isn't a perfect little stepford wife rules"Talk your son out of becoming a useless waste of space when he grows up :) Write your wife a lease tonight allowing her to reside on the property and have her take it to the pool tomorrow!!