Also, if you are looking for more value-add deals, REITs often don't play in the space (for better or worse).  

The question I have is the following: We have around $200k ($100k cash/$100k heloc) to play around with.

Nick, consider contacting @Amanda Han, she is based in SoCal, an expert in the field and active member of BiggerPockets community.

For instance, for school ratings, you'd look at greatschools.org, and for average days on market, you can use Rocket Homes. 

Since the properties are in an IRR, any investments into STR will be based on 1031 exchanges.

You will pay transfer taxes based off of the properties calculated assessed value, and if the property is in Philly city limits as your post location suggests, you're looking at a payment of 4.278% of that value being paid at close.

If you don't add your fee to the price investor will negotiate based on how much you are making on it. 2) I requested for her contract for it to have 10 days of an inspection period.

So im trying to figure out based on my situation what is the best move for long-term financial sucess.Now the rental is bringing in $800 net cash flow monthly, after all expenses are paid.

My concern is what he will do when he gets released, if the scenario plays as is being painted.The illegal occupier believes the system is broken, that he has rights over the land as a human being and told me he is willing to die for these rights.The police said they will have backup as they are concerned with the situation.

And, I would send notice of non renewal to the perpetually late resident, which is a judgment call based on my experience that late payers end up as non payers in many cases.