This seems the most seamless Option #3: I haven't found one but is there a hosting tool that collects payments and allows you to choose how to split it up and automatically payout property owners? 

Use it as a marketing tool and put the consequences of extremely high bills in the lease. 

@Gerry Magrini - Hi Gerry, as others have noted there are a lot of good tools out there that could be worth considering; but definitely look for a software solution built for DIY landlords (1 - 15 units) so you can bring some sense of automation to the rental management process (just to make things much much easier for you). 

Make your listing live once you have it fully furnished and have professional photos made.The Vrbo and Airbnb tools are all you need to get started self managing.We have a cabin in that area and we were just up there.

Quote from @Ryahn Toole: Hi Everyone, I'm starting off my journey into real estate investing this year hoping to get my first property in the coming months.

It can be very difficult to visualize sometimes and believe you can especially from most of society grooming you that you “can’t” or “come back to reality” or “let’s get back to work” for years and years…The power of the mind is a paramount tool to our individual success and everyone is likely always thinking too small for what we are ACTUALLY capable of…A very large impact way to really be able to open your mind and grow at a much more accelerated rate is to be around the folks that are always doing these things, and have already achieved what you want to achieve.

One for cleaning supplies, and one for maintenance issues (set of tools, stuff that cleaners don't use on a turn basis, but nice to have at the property).

Wondering what consensus is among investors here regarding various online tools and resources for market research, both local and national?

Is there any specific website / tool you use to estimate repair costs?

Yes, we have a blanket Google Adwords code on all sites which is used to track aggregate data and to populate clients dashboard w/ their websites stats w/o them having to even know how to use Google Analytics (saving them tons of time and getting them the data they need w/o the hassle)... but in order to get data down to the keyword (especially for PPC) we have to have each site connected to the Google Webmaster tools account that is verified for that domain and the adwords account for it.