I have put money into things like a necessary new deck, dry rot, new windows (they were only single pane), new flooring, retaining walls etc...just to keep it well maintained.  

These areas though show an affordable region to buy 3+ units and still retain a low vacancy rate. 

We painted inside, we painted outside and built a brand new deck, retaining wall, and path between driveway and front door.

The new work-from-home economy has people flocking to more affordable cities like Windsor while retaining their corporate earnings from big companies in Toronto. 

I would like to avoid buying the house outright before flipping it, so here's my creative flip that I'm looking for input on.What I'm thinking of proposing to the current owner is that he retain possession of the house, and we remodel the house and get it ready to sell.

My last couple I was basically forced to get an agent, so I retained 2 of my own tenants that are licensees. 

Problem is it'll reward the existing tenant and help retain a good one. 

Assuming that you could do all this and that the investment portion of your property makes up 20%, you have to weigh whether these contortions on tax returns and the fees that you'll pay revising taxes and retaining professionals is worth the $9,000 in tax savings (20% of $45,000).The short answers to your questions are yes, you can combine the 1031 exchange and the Section 121 exclusion. 

Ultimately, the title company won't make too much of a difference, your focus should be on retaining an attorney.

You're gonna learn a ton on your first deal, and the best thing you can do to ensure your success the first time around is to retain flexibility.Partnering up with equity partners will prevent you from dealing with the holding costs associated with a HML as well as the impending maturity - 12 months can go by faster than you think.