99$ a month is reasonable for bootstrapped company's. It's not reasonable for most hobby's, but 50$/month or 100$ / month are both rather high for a hobby website so there is little real loss.
I think HN has been collectively in denial on this kind of point lately. Yes, services offering real value should charge commensurate with that value. Yes, it's lovely if you're Patrick or Thomas and in B2B world where you can whack up your prices and hope whoever is paying the bill isn't spending their own money.
Newsflash: If you're dealing with a bootstrapped business, it might well be that the person paying the bill is spending their own money.
Newsflash #2: There are dozens of companies pitching useful-but-not-that-useful tools and services to these bootstrapped businesses. If you spend $100/month on this one, and $300 over there, and $150 on the next one, and ten more after that, and then you multiply it by 12... Well, before long you're spending on the same kind of level that it takes to hire some office help or to run a long-term marketing campaign with a significant level of funding or for that matter to hire in a guy who knows what he's doing for a few days to build your own customised versions of a lot of these services.
In short, if you think the ability to monitor a couple of production servers is worth $1,000+/year to a bootstrapped company, you're crazy. Yes, it's a convenience, but you're talking about a service that could be built using a couple of widely available building blocks with a tiny fraction of the running costs, and frankly to a business at that stage in its development it is highly unlikely that a server falling over until the morning is going to cause any real long-term damage anyway.
When you're dealing with relatively time-rich and cash-poor early stage businesses (OK, time-poor as well because they're trying to build the business, but that's not really the point here) you can't just dismiss the cumulative effect of all these SaaS gadgets. They add up, and if you want to know why so many small businesses fail, I expect not controlling costs is probably somewhere around #2 or #3 on the list.
Does that mean bootstrapped companies are bad customers for these kinds of services? Sure, maybe it does. If there isn't enough in it for both sides to make it a deal worth doing, it's not time to do the deal yet.
These costs are on top of whatever you're paying for the service itself, so if you're only going to be using the service for a few months anyway, you might be better off spending the time just implementing something quick and dirty yourself until you have a chance to do it properly.
The key thing is that in bootstrapping terms, very few of these services are indispensable: if you're in that environment then you're probably looking for just enough infrastructure to make a viable product/service, just enough legal/financial advice not to screw up in the early days, and then throwing everything else you've got into marketing, R&D, and sales to try and reach a self-sustaining level of income as soon as possible.
There are decent arguments for integrating certain services early on. For example, analytics/optimisation tools and billing services that boost customer retention can easily have a direct, significant, sustained impact on your income that exceeds the initial investment very quickly. But hardly any of these trendy SaaS tools aimed at small businesses are in that category.
Dozens? Seem low, I would say dozens each week ..