Here in my market we have to pay a separate line of taxes as well as go through a different registration process to do an air bnb. 

Don't get attached to a deal and keep emotion out.

It is a single family home with two separate houses on the same property and I got it at a very discounted price on an online auction, sight unseen.

Do they charge dump fees separate?

Losing tens, and sometimes 6 figures, worth of value can hurt generational wealth.I always like to ask questions before getting emotional just to ensure there wasn't something I missed on my end.

The realtor that has listed it is telling me that it is assumed all settlements are assumed to have completed and I would need to chase the PM and tenant separately to recover the cost.

One of my investment properties had two, separate plumbing issues (wthin 2 years of one another) that we filed claims for.

You cannot bring emotion into the transaction.

No, your loan underwriting will add those costs no matter whether they are escrowed or paid separately.

I generally separate site and hard construction and engage a General Contractor [GC] for the hard cost [vertical improvements] and a site contractor for the on & off-site construction.