Quote from @Chris Seveney: @Charlene Kingsnorth have you had an sec attorney also review what you are doing as if you're are having multiple people as part of a loan participating in it depending on the state this could get you in hot water - so be careful  good point Chris some state allow fractionalized deed of Trust mortgages other do not or require PPM like documents prior to offering them..

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

The past 3 people who did that have either continued to be demanding or have had their contracts "canceled" and I have to work to get the money in the long run.

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

I do know one of the people who works for me has a 2 year work permit (temporary) and she and her husband were able to buy a place in Alberta.BC and ON are very tenant friendly.

I have people who have been stationed there before, so I have a decent idea on areas to look in around the base.

I'm just beginning but am considering a bigger commitment in the next five years or so by accessing some or even all retirement funds to buy a building (I'm sure people have thoughts on whether or not that is a good idea!).

My father did this in Portland on two properties, for elderly people I think. 

You'll have a property manager do the management (so you being close to it is not needed).Yes there are risks for some people to go out of state but if you learn the techniques like I have, you'll see it's actually easier and far less risky.

Lots of people rent houses for parties as well, and you won’t be able to do anything about it.