I've truly been inspired by FT to try and make my business trips into fruitful ventures that I can reap on my own time (miles and points are paying for first class airfare and ten days in Hawaii). As such, I’ve made many of my business trips into mini MRs, taking a full day to go visit a client across the country due to segments flown or what have you. I’ve been impressed with my own results; mostly because it’s not my own dime.

But now, I, like many FTers, am going to attempt to do a true MR, one that is irrespective of the final location (well, I need to end up back home) and that doesn't get expensed. But I came to a wall last night when trying to put together a MR: How good is good? I've used much of the recommended software like ITA’s software, Travelocity's Dream Maps and the ultimate program IMHO, Flying Fish to put together a trip. As a money guy, I am always calculating the time value of money and factoring that into the kinds of MR that I could construct. But I need some benchmark for performance. The following scenario is based heavily on Flying Fish (and thanks to the person that created it! ^^^)

Last night, I spent about 3 hours trying to construct a MR and the best I could do was:
LAX-ORD-PHL-ORD-DEN-LAX for $228 and
LAX-ORD-DCA-LGA-BWI-DEN-LAX for $236

So both of these net me 4.7 and 4.13 cents for EQM and 3.9 and 3.52 cents for total miles, respectively. Personally, I don't think that's too bad but Flying Fish is telling me that I could do better (only $$ for total miles).

So my question is: How much better can it get and how often does “better” happen?
How much time do you spend before settling on a flight for a particular time period?
How often have you gotten $$$$ or even what I deem to be the coveted $$$$$ for a booking using Flying Fish? Am I looking at a Boston Red Sox World Series timeframe, once in a lifetime event or should a great price happen about as often as a delay flying into SFO? Are $$$ the most common type of MRs one gets? (Given that your status and booking class will net a traveler more total miles, we can focus the discussion on EQM or actual miles flown, not total miles. In this case, I only score a $ on all of my itineraries). I also am aware that most of the vets get their flights when price drops are announced but most of my flights are restricted to weekend activities because of my normal job and flights with coworkers where I should/must travel with them. I’m sure that will eliminate many of the cheaper possibilities. In that case, maybe some of you weekend Mileage Runners would be able to opine.

I understand that it comes down to what one is WILLING to pay for a flight. But ignorance, in this case, is not bliss; it means dollars out of my pocket and lost time that could've been better spent on finding better routings. If I know that seasoned MR travelers are always paying <3 cents per mile for their actual miles, I’ll keep pushing until I find something similar. But if ~3 cents is the norm, I'll be "wheels up" this weekend.

Thanks for the insight.

PS. I went through 6 pages of a search on the term “Flying Fish” to try and find a similar thread and didn’t find a similar discussion. If there is one, I’d be happy to be directed there.