I think if you interview a few Property Management companies you may find one that you both like and can trust with your cabin...and hopefully they'll be affordable and attentive enough to make you feel better about letting someone else handle your family cabin. 

Would I feel comfortable wandering outside of those few areas? 

I'm eager to go out and grind and make that first deal just have a few more things to feel comfortable about before doing so.

I feel like it would be fairly easy to get somebody in there paying $1400 a month.  

I feel if we sell our house to buy a bigger one, we will regret it down the road because of its huge potential. 

I have a feeling it may be the lender or the rep who doesn't seem to know the rules.CMHC will definitely approve a primary, even if you have 4 or 5 rentals.

Run it as a rental property and make the numbers work and if you like how the deal looks then offer the amount you feel will work.

My buddy just approached me with an offer to invest with him in buying foreclosures, he is a GC and he has done house flipping before, he wants me to invest 30K-50K of my own money and use it to get a 6 month rehab loan from a hard money lender at a little over 11% interest, after the House was finished we would split 50/50, he would also add me to his LLC that we would use for that future buy, the reason I’m thinking about investing Is bc I own my own business which will bring 200K this year in gross profits, the down side of my business is that I work 12 hour a day 5 days a week, and I feel that I’m slowly burning out.

Feel free to reach out with some basic details on the properties. 

I am currently in the market for my first property and live in the Metro Detroit area.I have found a few SFH's in Royal Oak that have caught my attention, as I feel they are being sold under market value based on comps I have received.