A person came by and was interested in renting it out and was willing to put some work in it.

Best way to find a lender is from someone referring from personal experience . 

I know the owner of Strawberry PM personally, and she sounds good, but I've never actually worked with her.Start by going to www.narpm.org to search their directory of managers.

If I have to boot someone I'll have it re-rented for more money in a week and the person getting booted will probably be living under the bridge as they won't find anything as cheap as me. 

Once you have those personal experiences from managing your own property, you will be able to identify and vet these property management companies when they're trying to make excuses of whatever the reason is as it stops you from achieving your objective. 

Feel like I'm using Guesty just to manage Airbnb.

Reece,without full financials i cant advise much, but i'd be leary if the deal doesn't pencil at least ok while the current rents are in place. reason being is you'll still have your expenses (PITI+mgmt+repairs etc) until the units can vacate, no rent remodel, lease up again. with that much repair it feels like you have a LOT of DD before diving in.

Feels like Partial 1031 Exchange would also be an opportunity, correct me if I'm wrong @Dave Foster, if you continue to rent out the property after the sale. 

I've noticed the forums provide a wealth of knowledge from individuals investing in a wide variety of strategies and feel this is the best place to start.

I personally have never seen that, but I’m only one person.