You can find they will lend 85-90% of purchase, and 100% of the construction with most programs charging 10-12% interest with 2-3 points.

So, I’m figuring it to be a wash between what the guest is charged and what I pay my cleaning staff.

If you find a property management company to manage an STR they will more than likely charge 10 - 25%.

Most engineers charge around $125 - $150 an hour - That's almost $10k.

The rents are below market, the current owner does not charge any rent for outside parking spaces, the parking garage rents are below market rate, there is a beautiful unit being used as an office that could command $900/month, storage fees are not implemented, water is being paid by owner, etc.

Right now my mortgage is 1650 and I am charging 1800 in rent (raising it 100$ in 2019).

The two options I have is for the full 12 months of the lease contract or the early termination deal I previously discussed with tenant of 3 month's rent plus any late payment charges. 

Unfortunately, I would say the owner is responsible for the expenses up front but can get reimbursed by charging more in the rent payments on the new leases. 

He doesn't charge any points and he is an avid investor himself.

Good ones are hard to find right now, and like to charge a bunch of money!