Sell, Hold, or 1031

[Michael Lyons]

My question is in regard to the 1031 exchange. I'll have 2 properties in this theory that i'll lay out. I am new to REI, so i'm not sure if this is even possible. If there's something i'm missing here please let me know, but i'm pretty sure i included all relevant information. Any and all comments or suggestions are appreciated.

Property #1:

•This was my primary residence for 5 years. It is now a rental

•cash-flowing $325/month

•it has 100k+ in equity at the moment and will have general not forced appreciation over the next 3 years, i am not putting anything else into it

•the mortgage is being aggressively paid down by tenant because it’s a 15yr mortgage

• i CAN utilize Homeowner’s Sale Exemption if sold sometime in the next 3 years.

•looking at a 39% return if sold in 3 years, using a safe projected sale estimate.

Property #2:

•Strictly a rental

•cash-flowing $335/month

•conventional 30yr amortization

•will be putting 60k+ into it over the next few years, which will moderately increase cash-flow, but will dramatically increase the equity.

•looking at a 15% return if sold whenever the work is done, using a safe projected sale estimate.

So my question is, should i:

1) sell Property #1 in the next 3 years to take advantage of Homeowner’s Sale Exemption

2) keep both and either cash-out refi or HELOC both (once i have more equity in Property #2) to obtain more properties

3) sell both at the same time via 1031 exchange to upgrade to a more cash-flowing multi-unit

option 3 is my main question, is that even possible? can you sell 2 seperate investment properties via 1031 to upgrade to another (obviously more expensive) investment?