Another example would be that "Roof Repair" seems to come after the sheetrock work - I would get the roof done before doing any drywall.There could be some regional variations on this, as well as seasonal variations.

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I have both of them in the trial period right now, which isn't actually that helpful because I can't see how everything works out without connecting it to current tenants (and I don't want to have them switch from service to service).

You should have seen the sinusoidal variation I had in the farm house floor we just did.Make sure you have an excellent grout mix or preferably an epoxy grout if you anticipate too much flexing.

There will be variation between singles and milti-families, aslo the city vs the suburbs.

I suppose technically you could even do some live streaming walk through feed.Looking to the intentions of the two types of loan investing, making the loan or buying an existing one, different variations of skill sets will develop.

You're talking about a variation of Cash for Keys. 

The real money comes from 1) up sells....and 2) people paying them to fill their CRM with leads and weed out the cream of the crap leads on a "30 day free trial basis", after which they will cherry pick and flip after you cancel your membership.

If you're going part time I'd say limit it to a 3-6 month trial to see if you like the work before quitting your job - it sounds like you have some savings and investments, so rather than be mediocre and stretched thin, it would be better to do it fully or not at all. 

I just did my trial and error and eventually found someone desperate to sell.