Obviously, I'd need to hire a property manager if I went this route, but I'm curious to hear the challenges, or benefits, that come with long distance investments.3) Is "retiring" and living off your rental portfolio a realistic goal? 

We are looking to arrange a place and time that would benefit us on the South Shore.

They're still considered capital gains but the STCG rates equal ordinary income rates.If the holding period is longer than a year, you will benefit from the long-term capital gains rates, which are significantly lower.Keep in mind, if you're flipping properties and are classified as a "dealer", the properties are considered inventory.

I know it all depends where you invest but we are looking around a $200,000 budget to start with.It seems the cheaper properties equals cheaper rents so just trying to wrap my head around how to make this a positive cash flow without having to run numerous smaller units.ThanksJennifer

Would that make it a prohibited transaction because I "personally benefit?"

Thing#2 - Use your owner occupant status to its full benefit (Low down payment-Lower interest rate, etc) and buy your next rental property now as an owner occupied home and live in it for a year or two while saving for rental property number three - Buy rental number three as an owner occupant and live in it for a year or two while saving for rental number four .... and so on.You see that your wife will need to be onboard for this to work out - You will be buying a home that is possibly not quite what she may have in mind for your "forever" home and there will be occasional moves as you acquire new investment properties - Eventually, you will not be able to continue this technique and you will get to buy that "forever" home.  

I researched like crazy over the last 2 days and after all income, costs, taxes including tax benefits, maintenance, vacancy costs, broker fee etc, I expect to get about $200 net income a month for the place.

I’m not so sure the benefits are as big as they are in the US given that as a trust director you’re still liable and the negative side is that trusts pay additional tax on land.This info is based only on a conversation i had this week so plase do not take as fact any of what i’m saying.

And it's awfully easy with a land contract to create a document that is so tight to protect the buyer that it crosses the threshhold of "risk of loss passing" which means that even though the deed doesn't change all of the benefits and obligations of ownership go to the buyer. 

The place will benefit from new kitchens and baths and I could raise rent from $2100 to $2500 easily.