And I do want to keep an investment property in the area to take advantage of the unique market here. 

Here are a few tips to consider on your journey.1)Find out where the local RE clubs are and figure out who is doing well in your market & who has been thru a few real estate cycles.2) Learn how to use a financial calculator (HP10bii) & how to apply it to investing.3) Study how to negotiate.4) Learn how to sell 5) Study Marketing6) Understand title 7) Learn how to value a property8) Nurture relationships with potential investors & private lenders9) Learn property management skills10) Make it mission to become extremely unique in your market on solving problems that will pay you well.

Nearly 100% of the prospects who approach my firm and DIYed their returns in the prior year are either preparing their returns in a materially incorrect manner or leaving advantageous strategy on the table.DIY software doesn't turn you into a tax professional any more than reading Web MD turns me into a medical professional.That said, if you are just starting out, you can probably get by self-preparing your return until you've reached critical mass and can absorb a rock star tax professional into your budget. 

Yes, your rates go down in the summer, but there are people who need a furnished rental for jobs/family/medical visits, so your property doesn't have to sit vacant when it's warm (okay, hot) outside.

Heated blanket kept tripping the breaker in her bedroom multiple times a time and requested we rewire the room to accommodate it as it was required for a medical condition.Had another tenant put in multiple requests convinced the property had ghosts or a past murder. 

Each tenant living in a building has their own unique rent amount, so even if they do not leave a notation with the rent payment, I know whom paid the rent based on the amount alone. 

I think house hacking gives you a unique opportunity to get a single family to cashflow. 

I own a medical office in a retail strip in West Michigan.

We pay materials and one guy 20 an hour and the other guy is a family friend/I pay him with medical care.

Tyler looked interesting since it seems rather stable (medical, university, community college, county employer, etc.)