I have seen some success with two things in the shoulder season to bump up weeknights.

You'll also be rewarded with a nice finder's fee and maybe even a small percent cut of the final development.Go out and rub shoulders with land owners - farmers, trusts, local RE meetups, local chamber of commerce, whatever.  

With a solid head on your shoulders you could pretty much make anything work for you.

Even if I am, I feel like October should at least have some shoulder season action. 

I don't want to Monday morning Qback every expense - first off I don't have the knowledge and also, it's tough to tell someone "handle it" - -and then want to look over the shoulder for every move.  

This is a shoulder season. 

Since my business model is focused on long term rentals, and we are able to secure a 3 month Security Deposit Guarantee through our unique placement process, the rental arbitrage takes the burden of an AirBnB not renting off of ours, and our owners' shoulders. 

In todays day of age it seems everyone has a giant chip on their shoulders about landlord and think everyone of them is the devil, so what can I do to protect myself and how do you spot people who are going to take advantage of you when screening for new tenants once that time comes?

Being 23 and actually having any long term goals at all puts you head and shoulders above the majority of people your age, not to mention you already own real estate and have plans to buy more.

Right now we are right back in the historical norm at about 64%.I think this spells big profits for real estate investors, because we will be competing with fewer retail buyers (who tend to pay too much) and there will be plenty of demand for rental units.Millennials seem to be good savers, despite shouldering high student debt loads, and working lower paid jobs as a result of entering the workforce in the recession.