New Cash into the PP with a VP Twist

[Bean]

So I have been using a system of each month buying all my assets back up to 25% and anything over 25% just letting them be.  However, I have part of me wants to go back to my speculative roots and start selling puts on the assets I want to buy.  Has anybody tried this?

Summary of what I intend to do.
1) Add to my cash position each month
2) Identify Asset Classes in my PP below 25%
3) Sell 1-2% ~90-120 Day OTM Cash Secured Puts for the appropriate amount to get me back around 25%
4) Rinse and Repeat for my accumulation phase.

Part of me thinks this is just a "fancy" limit order for what I am doing already and pays me for theta while I wait.

[AdamA]

So I have been using a system of each month buying all my assets back up to 25% and anything over 25% just letting them be.  However, I have part of me wants to go back to my speculative roots and start selling puts on the assets I want to buy.  Has anybody tried this?

Summary of what I intend to do.
1) Add to my cash position each month
2) Identify Asset Classes in my PP below 25%
3) Sell 1-2% ~90-120 Day OTM Cash Secured Puts for the appropriate amount to get me back around 25%
4) Rinse and Repeat for my accumulation phase.

Part of me thinks this is just a "fancy" limit order for what I am doing already and pays me for theta while I wait.

It all depend on what happens in that 90-120 days. 

[Bean]

It all depend on what happens in that 90-120 days. 

My justification to squeeze the theta premium out of this is I was going to buy the underlying asset anyways with a limit order.  The risk is I could lose out on upside, but I hate chasing a price up with constantly adjusted limit orders, it makes me feel like I am getting mugged.

[Xan]

Am I being hopelessly naive when I trade my PP securities with market orders?

[Bean]

Am I being hopelessly naive when I trade my PP securities with market orders?

I always use them, even when am ok with the market price, I just set the limit to slightly higher than the current ask.

Using market orders put you at the complete whim of the market makers or a violent market move. Why do that when you can limit your risk at no additional cost?