If you plan to grow and scale, break the bad habits now.

Maybe everything is fine but it's a good habit to not ignore red flags as an investor. 

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

I know there is no harm in building a relationship before I need them, but what should this timeline look like? 

you can take 20% to 30% off of that.. reason distance is affected by temps  terrain and driving habits ( lead foot LOL)  Plus you never want to run an EV Way down it affects battery life.. 

Are they currently habitability issues no, but if they fall on the home they will be.

Can you do something less drastic for say $10-$15k to make it habitable and livable and meeting lending requirements?

In retrospect, I was likely too forthcoming with the insurance companies.The house is habitable, there is no interior water damage, but many shingles have been blown off and the inspector and roofing contractors recommended a new roof or varying degrees of repair.

I mean even if you weren’t going to raise the rent I would get him out and get someone reliable with no bad rent paying habits in there.

They havent been harmed .