My point being is that I was lucky in the fact that I purchased my 4-plex at the right time and in the right market as it appreciated.

It took a little while to get them to trust me, but we've developed great relationships over time. 

I prefer buying during this time of year as the prices are usually lower and the competition is taking a nap because they generally do not want to move in the winter. :)Also, keep in mind that rent rates are also generally lower in the "winter" months so you may not get peak rent from your current home. 

I’ve done this method once before, but this time I’m a bit torn on the best approach.

There are programs, but they will never be as accurate as full and complete MLS data that you can map.

Although I believe I can see the path to my first rental easily, I'm having a hard time figuring out how I'd get to the next one. 

@Miriam B.yes Jack is currently a member of my land investing group so I communicates with him there and he answers questions about his training products and raw land investing in general when he has time.

Full renovation with new concrete driveway and new concrete walk out basement.

I hope that continues for a long time to come.

It's a very common mistake where an investor sold and bought properties and then when it's tax time they find out they didn't do the right process to actually qualify as a 1031 exchange.