From the date of the closing of your sale you have 45 days to identify your potential replacements and 180 days to close on one or more of those properties and complete the process.However, it sounds like this is your primary residence so it would not be eligible for 1031 treatment anyway.  1031 exchanges are only for investment property.  

Finally, have you factored in maintenance on the property?

How do you determine a selling price on a rental that is turn-key --- Are other formulas or factors involved for markup?

What are factors that can affect the market?

You may have more repairs and higher turnover rates, depending on your screening and how bad the area is, so you can factor that in.

I can't just sit around the house, so I am sure I will be doing something if I leave the 9-5, but I don't want to factor that unknown income in the decision making process.

@Keith Rorer I think it depends on a lot of factors specifically with the bank itself.

(It may make more sense to build new, BUT there are a lot of factors that go into it, like zoning and setbacks and what condition your existing garage is in and is there a loft space etc.  

You also have to factor in closing costs of the loan that will eat away equity. 

Due to this factor I don't think that conventional finance will touch the deal.