I have been narrowing down some markets and trying to explore/research more and network.

It has been on the rental market for about 55 days and the average in the area is supposedly 36.

Are the tenants paying market rents?

Plus, you already know the market, which gives you an edge.

Market Demand: Buyers love move-in-ready homes, and flips are often the most attractive properties on the market.

It is probably worth your time to connect with BOTH @John Warren and myself since we are both managing brokers, but John is more focused on property management and I am more focused on general contracting, but we are both Chicago investors as well.Oak Park and Lawndale are definitely two different markets.

However, the property’s cost basis (what they originally paid) carries over to you, meaning if you later sell, you may owe significant capital gains tax on appreciation.Alternatively, selling the property at fair market value eliminates gift tax concerns, but your in-laws may owe capital gains tax on any profit.

In fact, just finished one that I have yet to put on the market. 

I think it's the best market in the whole country in my opinion.

Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto.