Glad you were able to turn a hobby into a way to help you make some money after losing your job.
A Do you feel that running games for pay takes the fun out of GMing for you? If you made the money you need/want at your job, but the job wasn't so demanding that you still had time to run games for pay, would you?
B How does that work? If you have a slot from 6pm to 10pm and the customer cannot join until 7pm and doesn't tell you until the day or or several hours before, do you still play 4 hour or do you just play from 7pm to 10pm? If for a shorter period because of lateness, do you charge the same? Do you charge for no shows?
There was one instance where I had to miss a schedule session with less than 24-hours notice.. The DM didn't have a clear policy on no-shows, and payment method was to be discussed at the session. I just e-mailed him to say I couldn't make it and sent the amount for the session by Pay Pal. I don't feel right asking for refunds, prorating for fewer hours and missed session, or a credit for a future sessions. I can imagine that when you are starting out, one is much more willing to accommodate to build clientele and avoid bad ratings. But I imagine that even well established folks will find themselves being more flexible than is fair to avoid poor ratings.
C One thing that I'm concerned about with Start Playing is that payment is deducted at the start of the session. Maybe I missed something, but it seems that one could cancel up to the last minute. A more mature model is iTalki (a language-tutor platform) which has clear rules and mechanisms for this.
D Yeah, I think a little is a nice touch, but it can be overdone. Besides, most people are coming to play a TTRPG, not a video game, which hopefully keeps expectations reasonable. But as VTTs keep evolving, I fear things will get more like a video game. I wish more effort would go into smoothing things out, improving the GUI, smoothing the automating of area effects, etc. But cool spell animations make for better marketing.
E Let us know what you think of Start Playing. It would be interesting to hear impressions from the other side of the DMs screen.
I'm not sure how to divide your quote up, so I've added letters to reference:
A) Doing it for pay does change the dynamic a bit, and I find myself letting some things slide (etiquette, general leniency) that I wouldn't in normal games from time to time. It does put a degree of pressure on the situation, where as in my home game I might feel comfortable slacking on set up if I have had a busy week that isn't really an option. I also do my best to avoid missing any sessions, in a year and a half of weekly games only two have been called off on my account, one for a power outage during the session and one because I would be out of town.
If my primary income source was large enough that I didn't need/want the security of a separate income stream I could see myself still doing the paid DMing, but I would treat it as more of a gig job, with infrequency instead of a weekly schedule. For clarity: The only reason I started running a second campaign was the need for money, I would have rather become a player a couple of time over before I ran another game just because I don't get to be a player much. I do enjoy the paid games I run, it does change things a bit, but still enjoyable.
B) The normal slot is 9pm EST, it's a standing time and players confirm earlier in the day if they're still good to play, and at the end of each session we confirm the following week is okay. It's not uncommon for one side or the other to run 10-20 minutes late having to deal with kids, I just wait and talk with whoever is on time, or do extra prep if both sides are delayed.
I only charge for games that are attended, if someone pays in advance but then can't make it then the payment is just counted for the next session. When one couple cannot attend I simply run a one-shot with the couple that can attend. As the game is not through something like Startplaying, I'm not worried about ratings per se, I am more concerned about my current players remaining invested in the game and wanting to continue. Finding replacement players, that are not problem players, is a task I never enjoy and eats a lot of my time, as I no longer rely on this income (like I did when I started) I'm more flexible with things to keep the ball rolling, I value the income more as a separate income stream should something happen to my primary one (client issues, payment system issues etc. I get paid for the game through Paypal but my freelancing through Wise).
C) I think this is primarily an issue with pick-up games and one shots, and is best avoided by aiming for more players than the minimum. For example, I would consider 4 players a minimum for a paid group (unless the rate was higher), however, I would aim for five players as an ideal and be open to six. This is not a greed thing (mo' players, mo' money), but more about making sure that the game continues should one or two drop out or become flakey. I do see some games listed as up to 7 or 8 players and think that is purely extortionate, but that is because I don't believe you can reasonably deliver value to each player when the table gets too big.
D) I can only speak to Roll20 (I didn't like the look of Fantasy Grounds, and don't like the idea or business model of Foundry), there is wide scope for automating things through the API, such as automatically applying AOE damage and what not. It requires a lot more work for the DM and is something I'm learning slowly. The platform does improve incrementally, with dark mode and short rest/long rest automation being recent additions. The FX are just a fun aside really, maps are essential IMO for combat, even if it's just a white grid with some terrain hashed out with the drawing features.
E) I definitely will keep you all updated, when I get around to setting up my account properly there I think I'll be using it primarily for my arena-style games, the hard part is valuing myself enough to charge reasonable rates.