Still, if the cash flow is very little, or even a bit negative, but you can hold on to the property for 4 or 5 years, you will gain an average 20% net worth on said property that belongs to you and only you.There is a saying I love in the stock market, but I feel it also applies to the real estate market:"Time in the market always beats timing the market"This is to say that if you hesitate and don't pull the trigger for fear of having "missed the boat" you could be missing the boat that is passing in front of you.So, to summarize, I would look at other markets, but I implore you to look for a good realtor who can provide more than just the properties.

If he won't provide it he's not your marriage.

Right now I am seeing the biggest hurdle for people to get over is paying 55 to 100 thousand upfront, and may qualify for a loan if one was able to be provided. 

While they might not provide the highest ROI, if you're looking for a more lifestyle-oriented investment, there are options available that offer full ownership with returns covering expenses and could provide cost-free vacations for you and your family.I would caution against most timeshares, private residence clubs, and fractional programs, as they often come with limitations and challenges in resale.

My family and I vacation frequently around the Traverse City area and would love to have a place that we could use part of the year and also would provide some additional income. 

When I ask for something in writing they are unable to provide this claim. 

House hacking usually provides returns above and beyond any other asset class and is a great low risk way to get started.

Can anyone provide recommendations on great courses or other resources to fast track my knowledge of landlording.

All these are estimates as you have not provided some of the information.Now let's look at any positives you have.  4.2% INTEREST RATE!  

Regular meetings, workshops, and events are frequently held by these associations, providing an opportunity to network with seasoned investors.Real Estate Conferences: Participate in Chicago's real estate seminars or conferences.