There are two issues here, if I understand correctly. One issue is players who are DFA'd. So, make DFA not allowed until after R5. Easy to check compliance. League Transactions > Designated, for all teams. Must waive or release only instead of designate. The second issue is what to do with FA's signed before R5 and not assigned. I'd be OK with a 20 man roster + ML FA signed, but not assigned, before R5. The 20 roster spots would be filled by players from previous season. There will still be bidding wars for the best players and there won't be a lot of bargain players that early in FA. Too hard to police otherwise.

Designated = the same whether or not you do it with waivers. Thus the transaction list on its own is not enough.

2nd part we seem to be onside with

Settled, and put on the front page.

Your 20 man roster would be achieved by;

DFA with waivers (minors or majors)
Release (either minors or arb eligible MLers)
Signed MLers not assigned to the 25 man

We're singling out the DFA without waivers because that's a loophole that could pull someone off the 40 man, then be reassigned after Rule 5 without anyone but the current team having access to the player.

BTW, I will manage the enforcement of the rule, whether commish or not.

Back to 16 in; half a league.

This intrigues me.. I would be down for a team if you need another.

You're in. 17 on the list.

It's intriguing....I like the idea.  I'm concerned with the mechanics of it....

For example, suppose your settings in R5 give you 18 pitchers out of your 20 picks (if you're picking to fill out your 40...what then?  When you combine available options, needs etc. it could mean total disaster with respect to MWR, etc. 

Not that it's a bad thing.  It's a very heavy penalty to anyone who doesn't have a really really good handle on how HBD works.  Then again it could result in an extremely busy trade market.  That could be a good thing.  Just kinda noodling out loud.

All that said, I would be up for the challenge.

Ok, you're on.

Yea, my main worry is that reminders get out to change the draft number off of 0, and the max salary gets changed from 327K

Everything else to me is good for giggles. 
I also think you have a very busy FA market, because that's buried of the 20 man for the first season. But, you sign 5 years, and that's taking up 1/20th of your team for 4 years, unless you have the freedom to DFA him off.

Whole bunch o' things.

If you're letting someone in who can't handle the basics of the R5, you're doomed.    Just an opinion. 

I don't disagree with that.

My concern has to do specifically with draft settings. You have to run a rule 5 draft differently I think because your needs will be more position specific. One mistake in your settings and you're in trouble...unlike the amateur draft where it's easy to recover.

Draft prep time will be compressed also..should be fun

That's the only downside I see to this. If R5 happens to occur on a day when you're not available to prcepare for it, your season can get ******.

I can see that.

Is anyone in a pre season position right now? I think you can address the settings part anytime up to Rule 5 draft, which means that the draft list order would be the issue if you missed that day.