I purchased both as a package and for the next six years enjoyed great cash flow as I paid the tax on the house lot annually at about half of what it should have been and neglected to pay anything on the tennis court lot.  

Coin jams are going to be your second biggest headache unless you invest in those fancy ones with tap-to-pay but those cost a pretty penny.

A property is only worth what people can afford to pay for it. 

If you can get all the bedbug containing furniture out of the place and it will sit for awhile (or let it sit while the other repairs are done) you may be able to avoid some cost, but if you want to get a paying tenant in sooner rather than later you will want to bite the bullet and get it well done.

I took the next 5 months to tackle everything myself spending approximately 17k in supplies and tools + paying a plumber and roofer 4k total to fix those issues.

IE securing them paying tax's insurance etc etc. 

If someone doesn't pay their rent, then it can take over a year to evict them, and then I'd be left paying that mortgage and fees for a lawyer, etc.

You can pay for expediting for plan reviews and the best way to "expedite" beyond that is to make sure that your engineer / consultants are submitting complete packages each review cycle.

Most brokerages will pay around 25% of their commission when you refer a buyer/seller.

Plus, you have to pay the cost to be the boss.