First,if I were to share this dilemma with my wife, she would, matter of factly, say "I did not know my husband could be bought." 

Also, once you get in the swing with the company it doesn't really matter as they pay out on the same schedule.  

I want to recap what you're asking because it was a little confusing and it matters a lot.I think you want to sell your property and buy new so it can give you some cash out and meet your goal of $2k income per month. 

@William HutchinsonIs one worth it … yes / no… scale matters but so does starting. 90% of us start with one.

I would say that any deal that makes money (no matter how small) AND provides lessons learned is not a base hit but is actually a HOMERUN!

To make matters worse, millennials also comepte with boomers who want to downsize.A lot of things can impact a market, rising rates is probably the biggest risk right now to slow down price appreciation, but overall, neither the supply nor demand are going to change substantially - we just have more people than roofs.

The time of the season doesn't matter, yes people are more likely to be looking for homes in spring and fall but somebody (even good tenants) are looking for housing in the winter months!

Changing your plans like backing out of conventional financing last second will most likely hurt you.Every lender is different, but you'll probably need the seasoning period no matter how you buy your house (cash, financing, etc).It's always more expensive to renovate than you think.

Speed matters a lot in this business4.

It’s just a matter of positioning your property correctly for the right type of tenant.