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've mentored so many wholesalers and the ones I've seen success in have build tight knit networks instead of trying to be the jack of all trades and taking their deal to everyone on the internet trying to squeeze out a few more bucks.

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. 

@Nathan G.Sadly, the reality of a landlord's having to maintain their reputation in a small town or in a close-knit neighborhood, in the age of social media, has expanded to many larger communities.My first impulse would be to set out the facts of the matter from my perspective, along with the appropriate documentation.

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.