Some more technical insight would be helpful in developing a purchasing criteria.....I.E. how much flexibility do you really want, and what exactly do you envision using the scope for? What is day to day for me, might be considered "minority" for others...
I can say what I am doing today and what I hope to be doing in the future. At the moment I am designing power related products for industrial/professional imaging systems. This generally means low voltage - medium current from multiple sources being distributed to multiple outputs at various voltages. All of this is managed and monitored with a blend of analog comparators, 16bit A/D, MCU's, i2c, SPI, 1-wire, boost converters, buck converters. I need to see the low mV drop across a resistor compare with an i2c event. Maybe monitor a comparator input to gate timing on routing FETs. Converter design has me looking at shaping the PWM gate pulse while monitoring noise/ripple at various loads. All of these things are normal measurements for most anyone. There are so many things that I am not capable of doing with my limited equipment on my bench right now so I hardly know what to hope for in a new scope. Triggering on digital data would be a great benefit. Right now, trying to temporally tie a Rigol scope with a Saleae logic analyzer is very time consuming. Looking for a specific i2c command and understanding it relationship to an analog event is a pain. Window testing sound really great. As the circuit switches from one power source to another at full load, it can only drop so much before things go bad. That is a simple measurement, but some effort involved in comparing to a previously known good waveform. Some of the advanced math functions I see in the higher-end are outside of my understanding. I would like to learn more about why various math options exist and how they can be used in analysis and understanding of the signals.
For the future, I have been studying FPGA dev for the purpose image transformation. This will bring a whole new crop of measuring challenges that I am not even aware of yet. Hopefully the scope I choose today will be enough to get me through the learning curve and at least to the point where I can release my first FPGA device. The cost of developing a new product will involve way more than just a scope and an FPGA dev environment so I am hoping that I don't have to buy a new scope right at the end of development when cash is super tight. If this happens, I will be presented with very fast serial signals at 3gbps+ and I am thinking of renting a scope for that period of development if possible. There is not a long term need to monitor the serial signals beyond knowing that they are properly making their way into the FPGA and back out. After that is worked out, I would be back into the slower parallel world for oscilloscope measurements and the images will be measured on dedicated image monitoring gear - totally separate from an oscilloscope. It's really hard to understand what I may be needing for a project like this.
Clearly I am looking for a general purpose scope that will be the least likely to limit my design options in the near-ish future. I would be happy if it was relevant for 3 years but that is a random guess. There is no real way to understand how long it will be before the scope limits my progress. Therefore, I would like to choose something that is significantly more advanced than I need today while not being such a financial burden that it slows down the business. The 'upgradable' scopes seem interesting because I can spread the cost out and choose what I need exactly when I need it. For the moment, I am guessing what the future may bring. I know that I could get everything I would ever need for $30k, but that would mean I would be a slave to the scope for a while. I am also building a small P&P line and spending about $10k+ on other bench gear so I definitely need to balance the budget wisely.
Beyond cost, I am certainly worried about the day-to-day experience and ease-of-use. If two scopes are the same purchase price with nearly identical features, but one is a little slow and cumbersome - it may double or triple the cost of that scope over 3 years in labor and missed opportunities. Intuitive is just as critical as bandwidth IMHO. I have learned that lesson in my CNC shop over and over.
That is VERY similar to the type of work I do. DO NOT underestimate the need for bandwidth. I think a lot of engineers falsely assume that "because my SMPS is below 1MHz, I don't need anything more".
Nothing could be further from the truth. You need to consider the ability to analyze feedback loop interactions and external resonant tanks. Do you need to go out into the GHz ranges? chances are no, BUT it really depends on the interaction between your devices, and the PCB (often overlooked).
FPGA are very sensitive to step responses, and although most HF artifacts in POL/SMPS are very low in energy, they can cause instability in the sense loops of many POL devices. These problems can lead to inefficiency and can also lead to thermal issues. Especially devices that have large current ripple.
The other consideration (often overlooked) is the rise time of highly critical signals. Especially in shared system buss architectures. Remember that bandwidth on the front end also relates to rise time.
I think you would be selling yourself VERY short if you didn't look at these very real scenarios. I have been there quite a few times. Everything will seem fine, until you have an UN-explainable problem. Then you are really going to wish you had the ability to properly capture fast, erroneous events.
The next MOST critical factor, is your probing solution. In fact I would be willing to say that your probing solution is MORE important than your acquisition device. As with most things, the weakest link in the signal chain will dictate your results.
Another consideration is the use of ext Vref. Do you have a meter spec'd that is appropriate for calibrating Vref for a 16 bit A/D? Also do you have a calibration reference for all of these tools?
The next question would be about clocking solution. What are your plans for clocking? The MCU's and other devices are going to need to lock to something external.....and using GPIO pins for PWM on a micro is just not going to work out. You will be looking at max PWM of around 500ish HZ. I am assuming you know of that quite well already, and would be using serial i/o for switching, BUT this is generally not a good way of doing this. You will need to be able to respond to external errors (based on sensor f/b) much faster than the MCU can provision for. I have tried many experiments on multiplication of MCU PWM, with mostly unacceptable results.
I could go on and on here about WHY more bandwidth is necessary (beyond 100 MHz) but obviously there is a limit. I think a 300-400 MHz front end is MUCH more appropriate, and most tools that you are going to consider and NOT going to offer "upgradeable" bandwidth. Consider this...."upgrading" bandwidth simply means that you ALWAYS had the front end to begin with, and that the manufacturer has simply crippled it, in order to get more $ from you.
If I was in your situation I would rent or lease some "high end" tools....and do some comparison. Analyze some of your signals at both 100 MHz and then at 400 MHz or above. You will gain some serious insight into just what you are missing in the lower BW device. Also the probing solution is CRITICAL, I can't stress this enough. If the properties of your probing solution create resonant tanks of their own, you are really flying blind. Also consider the dynamic range of the probing solution and front end. You need a solution that can respond to extremely fast state changes and can resolve the step response of your power devices. FPGAs are tricky that way...
P.S. one important thing to note is the usefulness of FFT based operators, in characterizing shifting impedance vs frequency.....you obviously need a front end that can acquire pesky harmonics (or fundamentals) but ALSO need the sample rate to makes sense of it. Since FFT resolution and bandwidth is proportional to half the sample rate of the acquisition device, you aren't going to find many options in large sample rate, low bandwidth scopes.....do you really need to look out to 5GHz+ for oscillation/resonance in your step response? well no i suppose not, BUT you might miss harmonic interactions in your switching devices, that can cause errors in proper voltage regulation.....
I could post a screenshot of a budget scope FFT (DS2102A-S) vs the WR64MXi....showing the exact same signal (from a POL). It will clearly show just what you would be missing (in the signal interpolation) between the decreased bandwidth (and crap probing solution) of the Rigol unit, and the increased bandwidth (and proper FET probing solution....).
Obviously it's an apples to oranges comparison....and that is the point. The proper way to do that comparison would be with differential probes and a well engineered test, but the differences in captured data are SO SIGNIFICANT, I think the problems will be immediately obvious.
Harmonic content in your step response, with complex digitally controlled POL devices, is CRITICAL in properly driving dynamic loads.....I can't think of a more picky dynamic load than a modern FPGA/ASIC/SoC
Also these harmonic interactions and large current oscillations (as a byproduct) can cause massive premature damage to multilayer SMD caps....and if your sensors are sensitive to harmonics and those physical resonances/harmonics are existing on the same PCB/plane...well you know where this is going.....you will get huge instability and oscillation down the line....this can even go as far as LF resonances that will easily destroy the inductor of some POL devices.....not to mention the power lost.