However, now that I have my primary residence paid down a little more I am interested in giving myself more financial freedom in the future and I am interested in buying and holding multi-family properties.

In couple years we are looking to purchase a house, would it be sufficient for our landlord to provide a letter to our future lender that we paid on time?

One tenant still has not paid September rent.  

Maybe this is why the rehabber paid what he did...

Starting earlier means that you start the mortgage pay down sooner if you Buy and Hold and therefore your properties are paid off faster as you get older.2.

I would definitely submit a complete offer package with dates, terms, numbers, copy of an earnest money check, proof of funds, or pre approval.

We paid $220,000, and rented out the whole house for $1,650, which was high for Orillia.

But having your license can sometimes be a bad thing if (and more likely, when) a deal falls apart long after you assigned, and the seller/buyer get "lawyered" up to try to get the assignment fee that they paid you a long time ago (even though your one and only obligation in the deal was to assign your option to them, and you have no further liability/obligation after you assign.

I have no problem paying what needs to be paid tomorrow and next month if I have to, working as an engineer has blessed me, so the money issue is not there.

most will pre-qualify you for x amount.