re #2: Yes, many notes have the provision to make sure the investor gets a 1x preference on dollars invested (some preferred and some common for their investment.) and this is, IMO fair.
re high resolution financing: if you are offering different investors at different prices, you are likely to make your investors less than happy with you.
re less control and no board seats: in my experience, having a board correlates strongly with success. so i think this is a negative. to put money where my mouth is - for my last startup, I took a board even though I did not have to.
re raising a few hundred thousand or less: in my experience, strongly correlated with startup death.
re high res financing: closing dates can also vary in addition to cap. i've personally experienced varying closing dates with same cap and the initial bit was much needed at the time. haven't experienced priced yet but can imagine process being a bit slower.
re less control and no board seats: agreed. though i think it depends on the board member. in your case, i'm sure he was top notch :)
re raising few hundred thousand or less: hmm, don't have enough data. but uber's initial round was $200k. https://angel.co/uber
Uber was cofounded by someone with a large exit. This number does not represent the actual finances available and is likely misreported. I have a single exception to the low initial raise as well. Still anecdata and does not really refute the point. There are successes, but there are way, way more failures; early investors hate to reinvest pre-traction.
re high resolution financing: if you are offering different investors at different prices, you are likely to make your investors less than happy with you.
re less control and no board seats: in my experience, having a board correlates strongly with success. so i think this is a negative. to put money where my mouth is - for my last startup, I took a board even though I did not have to.
re raising a few hundred thousand or less: in my experience, strongly correlated with startup death.