In particular, is there any software/tooling which is typically used to analyze & find tenants, analyze deals, and used to find a local realtor who specializes in real estate investing?

The area off Broadway now known as "THE war zone of all war zones" was previously known as "THE fur district" and the area was all top shelf, opulent mansions. 

There are tons of software to choose from.

So, you'll want to use tracking software like Hubstaff to monitor what an RTM is really doing. not as much of a concern with a VA if you pay them for performance and not by the hour.- Getting an RTM to buy into your ompany culture.

Has anyone found an excellent software to manage these transactions.

2) Grace Period: 5 days- Many judges in our area frown upon no grace period- Ours is voidable if tenant is late more than 3 times in a 12-month period3) Late Fee 5% on the 6th- Our software auto-charges- We will waive for a GREAT tenant, 1 maybe 2 times annually, just like a lender may waive the occassional late fee4) Daily Late Fee: 10% per diem- Our software auto-charges- We added this years ago when a smart aleck tenant, upset that we wouldn't waive their late fee, told us they would pay the last day of the month.- Judges often throw these out:(5) Eviction Notice for Nonpayment of Rent: sent ASAP- In Michigan, it's a 7-Day Notice- Our staff bulk sends on the 6th of each month, no exceptions- Even our best tenants get them and we just tell them it's automated and they can ignore if they payRecommend you have a detailed Eviction Procedure and follow it!

I'm not sure if there is a creative way to accomplish my goal through that software that is integrated as well.

I'd speculate that your CPA failed to check the "complete disposition of activity" checkbox in his tax software, keeping these losses locked instead of releasing them.2.

I'm co-owner of a small 2 man software dev shop. 

It seems like the condo you linked is almost geared towards short term rentals, so you should be in the clear on this specific situation. 2) I would take a look at some STR data either via a dynamic pricing software (pricelabs, wheelhouse, etc.) or take a look at Airdna to take a look to see what is the “sweet spot” is in terms of size of rentals in your market.