If tax returns and DTI is an issue look at private institutional lending. 

Or is it a community specific thing?

According to the Fair Housing Act and the Americans with Disabilities Act:Even if a landlord has a no pet policy in place, the law does not consider service animals as pets and therefore the service animal is exempt from such a restriction.Service animals are allowed anywhere a person would go, including food areas that would normally restrict an animal’s presence.Landlords cannot charge a pet deposit or pet fee for service animals, however the tenant is liable for any damage that the service animal may cause.Landlords can require written verification from the tenant’s health care provider that they are disabled but cannot ask for any specifics about the disability.Landlords can require written verification from the tenant’s health care provider that the service animal is needed.Landlords can request copies of the animal’s health records to prove the animal is in good health, parasite-free and immunized/vaccinated.Landlords can write warnings or even evict a tenant with a service animal if the animal is disturbing others, posing a threat to others or causing considerable damage to the property.In other words, you can ask for appropriate paperwork concerning the tenant’s need for the service animal and to verify the animal’s health. 

Are there specific networking events, online platforms, or strategies that have proven effective for building relationships with investors?

As an owner, what are the top considerations or issues you face when deciding to bring on a property management company to help manage your units?

I am by no means an attorney and to my limited knowledge I don't know of anyone who has gotten "caught" with the new illinois law, but my understanding is that you can not "Market" (aka sell side of wholesale) more than one property per year.So if you had a licensed agent do the "marketing" of the property once it's under contract then you should be in the clear.You can of course double close, but the law is more specific to the marketing of the property vs. how it's closed.My suggestion @Andrii Sazhnev would be to find another wholesaler who has their broker's license to work with them while starting to get your license...in my opinion (if you have the time) it is worth it for anyone who is doing real estate full time to get there license - simply for the education and MLS access.

The owner attempted to fix the issue but tore up the drywall and couldn't locate the source of the leak.

Here is the issue below. 

Oregon has strong tenant protections, and staying compliant is essential to avoid legal issues down the road.There a two major places to get forms and education. 

So, if that might be the reason why you're having an issue perhaps hire the most local yokel contractors/tradesman you can find.