Any insights or guidance would be greatly appreciated!

Hey there @Isaac Watson,It's a great question. 

I’m also open to any schooling required to be considered for a specific role. 

Has anyone had any experience with their repair services?

This is not the case for the majority of metro areas across the US.In less hyperbolic markets there wasn’t an intense amount of speculation so operators didn’t pay high and are weathering the storm on interest rate resets and are finding a way to refinance Deals with maturity walls.I am finding that a lot of killer deals with my clients are happening in the sub 50 unit deal space for those who need to sell, because there’s much less competition in a chase for yield.  

The only thing about it is that the property hasn’t been very well taken care of, so we know there’s a lot of work to do to fix it.

Learning how to properly evaluate a rehab budget is imperative to your success and there are many books and posts on this topic of how to do it - I have posted many on this topic in the past.Don't forget on your list windows/doors, trims (baseboards and door casings), waterproofing/protecting floor of garage, potential need to frame/or upgrade farming of exterior walls of garage (many garages have stem walls) and the flooring is often sloped to garage door so leveling the floor may be necessary.

The planning staff should be able to walk you through any options for zoning changes or variances if there's a way to make short-term rentals work in your case.

Tenants are a crapshoot in the end either way.

Seems that you are most focused on property taxes at the moment, but all of them really need to be evaluated for a complete picture.