Would love to connect and pick your brain on this strategy.

This thread is picking back up here:  https://www.biggerpockets.com/forums/49/topics/698208-connected-investors-pin-tool?

However, it seems like there are so many rules and regulations with the State/City and when it comes to getting approved to list on Airbnb. 

It needs a lot of work, and I plan to convert it back from the single-family home it is now to the two family home that it is still listed as on the title.

Check out similar listings in your area, see how they're doing, read reviews, and snoop around the pricing.

I was not aware of Tim before reading your post, and he's now at the top of the list after some research and listening to podcasts.

Feb marked 3 months in a row of the market picking up.

My question is as the co-cost/listing manager what protections do I need?

And the answer is always the same :-) There is no way to accurately do this...too many variables and moving parts, plus it varies too much from one locale to another.You need to find a really good General Contractor and pay him to walk the property with you....over and over....until you feel really comfortable estimating yourself, and that should take years.Alternatively there are online calculators (even one here in the tools section) but I would not rely on them for the reasons listed above.

.;-)I would pick the strategy where you have the best chance at having mentor/team/knowledge/experience and closer to turn key.